scholarly journals The total synthesis of D-chalcose and its C-3 epimer

2013 ◽  
Vol 9 ◽  
pp. 2620-2624 ◽  
Author(s):  
Jun Sun ◽  
Song Fan ◽  
Zhan Wang ◽  
Guoning Zhang ◽  
Kai Bao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Camphorsulfonic Acid ◽  
Asymmetric Dihydroxylation ◽  
Key Steps ◽  
Stereogenic Center ◽  
Hydroxy Groups

We completed a new and efficient synthesis of D-chalcose (I) and the first synthesis of its C-3 epimer (I′) in nine steps with overall yields of 23% and 24%, respectively. The key steps in the sequence were the formation of the stereocenter on C3 via Grignard reaction, the introduction of the stereogenic center on C2 by Sharpless asymmetric dihydroxylation, the protection of the C1 and C2 hydroxy groups with tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf), and the selective cleavage of the primary OTBS ether using catalytic DL-10-camphorsulfonic acid (CSA) in MeOH.

Concise asymmetric total synthesis of bruceolline J

2015 ◽  
Vol 2 (5) ◽  
pp. 548-551 ◽  
Author(s):  
Dattatraya H. Dethe ◽  
Vijay Kumar B
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Asymmetric Total Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

Concise biomimetic and asymmetric approach involving Sharpless asymmetric dihydroxylation and Lewis acid catalysed cyclopenta[b]annulation as key steps to synthesize (+)-bruceolline J.

Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach

2014 ◽  
Vol 12 (31) ◽  
pp. 5973-5980 ◽  
Author(s):  
U. Nookaraju ◽  
Eeshwaraiah Begari ◽  
Pradeep Kumar
Keyword(s):  
Total Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Novel Synthesis ◽  
Key Steps ◽  
Julia Olefination

A simple and novel synthesis of (+)-monocerin was achieved from 3-buten-1-ol employing HKR, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation–cyclization as the key steps.

Total synthesis of zincophorin

2005 ◽  
Vol 77 (7) ◽  
pp. 1131-1137 ◽  
Author(s):  
Janine Cossy ◽  
Christophe Meyer ◽  
Magali Defosseux ◽  
Nicolas Blanchard
Keyword(s):  
Double Bond ◽  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Naturally Occurring ◽  
Key Steps ◽  
Stereogenic Center

A total synthesis of the naturally occurring ionophore zincophorin has been realized. The key steps are an intramolecular oxymercuration of a cyclopropanemethanol for the elaboration of the tetrahydropyran ring and a Carroll–Claisen rearrangement to control the configuration of the double bond at C20–C21 as well as the stereogenic center at C21.

Total synthesis of natural quadrone

1988 ◽  
Vol 66 (3) ◽  
pp. 528-530 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Montse Llinas-Brunet
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Efficient Synthesis ◽  
Camphorsulfonic Acid ◽  
Natural Form

Starting from the ammonium salt of (–)-10-camphorsulfonic acid (4), an efficient synthesis of quadrone (1) in natural form has been accomplished.

A stereoselective approach to indolizidine and pyrrolizidine alkaloids: total synthesis of (−)-lentiginosine, (−)-epi-lentiginosine and (−)-dihydroxypyrrolizidine

2014 ◽  
Vol 12 (25) ◽  
pp. 4454-4460 ◽  
Author(s):  
Shruti Vandana Kauloorkar ◽  
Vishwajeet Jha ◽  
Ganesh Jogdand ◽  
Pradeep Kumar
Keyword(s):  
Total Synthesis ◽  
Pyrrolizidine Alkaloids ◽  
Starting Material ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

The total synthesis of (−)-lentiginosine, epi-1,2-lentiginosine and dihydroxypyrrolizidine is reported from an aldehyde as a starting material using organocatalysis and asymmetric dihydroxylation as key steps.

Total synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate, a major component of the sex pheromone of the stink bug Edessa meditabunda

2020 ◽  
Vol 18 (26) ◽  
pp. 5034-5044
Author(s):  
Daiane Szczerbowski ◽  
Stefan Schulz ◽  
Paulo Henrique Gorgatti Zarbin
Keyword(s):  
Sex Pheromone ◽  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Grignard Reaction ◽  
Stink Bug ◽  
Synthetic Route ◽  
Key Steps

A convergent synthetic route was developed for the stereoselective synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate. The Fouquet-Schlosser variant of the Grignard reaction was used as key steps.

An efficient synthesis of (+/-) cherylline dimethyl ether

2009 ◽  
Vol 2009 (8) ◽  
pp. 482-484 ◽  
Author(s):  
A. Sanjeev Kumar ◽  
Samir Ghosh ◽  
Kale Bhima ◽  
G.N. Mehta
Keyword(s):  
Dimethyl Ether ◽  
Sodium Cyanide ◽  
Single Step ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Reaction Conversion ◽  
Key Steps

A concise route for the synthesis of (+/-) cherylline dimethyl ether is reported. The key steps involved are Grignard reaction, conversion of alcohol to nitrile using (N-( p-toluene sulfonyl)imidazole and sodium cyanide), reduction of the nitrile intermediate followed by Pictet–Spengler cyclisation and reductive N-methylation in a single step to provide cherylline dimethyl ether as a racemate.

Total synthesis of wikstrol A and wikstrol B

2019 ◽  
Vol 17 (35) ◽  
pp. 8206-8213 ◽  
Author(s):  
Kui Lu ◽  
Ming Li ◽  
Yuna Huang ◽  
Yuanyuan Sun ◽  
Zhi Gong ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

The first total synthesis of wikstrol A and wikstrol B was achieved via Sharpless asymmetric dihydroxylation, Sonogashira and rhodium-catalyzed oxidative coupling as key steps.

Chemoenzymatic total synthesis of ent-neopinone and formal total synthesis of ent-codeinone from β-bromoethylbenzene*

2011 ◽  
Vol 89 (6) ◽  
pp. 709-729 ◽  
Author(s):  
Jan Duchek ◽  
T. Graeme Piercy ◽  
Jacqueline Gilmet ◽  
Tomas Hudlicky
Keyword(s):  
Total Synthesis ◽  
Heck Reaction ◽  
Aldol Condensation ◽  
Side Chain ◽  
Prins Reaction ◽  
Toluene Dioxygenase ◽  
E Coli ◽  
Key Steps ◽  
New Compounds ◽  
Stereogenic Center

Formal total synthesis of ent-codeinone and ent-codeine was accomplished via the total synthesis of ent-neopinone attained in 14 steps from β-bromoethylbenzene. The key steps included (i) enzymatic dihydroxylation of β-bromoethylbenzene with E. coli JM109 (pDTG601a), an organism that overexpresses toluene dioxygenase, (ii) a Heck reaction to establish C-13 stereogenic center, (iii) aldol condensation, and (iv) 1,6-conjugate addition of the ethylamino side chain to C-9. Several other modes of construction of the C-9 and C-14 centers were also investigated: Mannich cyclization, and aza-Prins reaction. The synthesis of ent-codeinone was formalized by intersecting Fukuyama’s recently published approach. Experimental and spectral data are provided for all new compounds.

Synthesis of the C19–C30 Bis-THF Fragment of Iriomoteolide-13a via Stepwise SN2 Cyclization and Intramolecular syn-Oxypalladation

2020 ◽  
Author(s):  
Hui Zhao ◽  
Kai Gao ◽  
Haichen Ma ◽  
Tsz Chun Yip ◽  
Wei-Min Dai
Keyword(s):  
Aldol Reaction ◽  
Allylic Alcohol ◽  
Asymmetric Dihydroxylation ◽  
Hydroxy Groups

The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The w-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by <i>anti</i>-aldol reaction and asymmetric dihydroxylation (AD). Upon heating in pyridine the stereotetrad underwent an S<sub>N</sub>2 cyclization to form the C19–C22 THF ring. It was followed by an intramolecular <i>syn</i>-oxypalladation of the C28 chiral allylic alcohol to give the C23–C26 THF ring.

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