Enantiospecific Synthesis of Optically Active 6-Methoxytryptophan Derivatives and Total Synthesis of Tryprostatin A1

1997 ◽  
Vol 62 (26) ◽  
pp. 9298-9304 ◽  
Author(s):  
Tong Gan ◽  
Ruiyan Liu ◽  
Peng Yu ◽  
Shuo Zhao ◽  
James M. Cook
Keyword(s):  
Total Synthesis ◽  
Optically Active ◽  
Enantiospecific Synthesis

ChemInform Abstract: Enantiospecific Synthesis of Optically Active 6-Methoxytryptophan Derivatives and Total Synthesis of Tryprostatin A.

ChemInform ◽  
2010 ◽  
Vol 29 (20) ◽  
pp. no-no
Author(s):  
T. GAN ◽  
R. LIU ◽  
P. YU ◽  
S. ZHAO ◽  
J. M. COOK
Keyword(s):  
Total Synthesis ◽  
Optically Active ◽  
Enantiospecific Synthesis

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

ChemInform Abstract: Total Synthesis of Natural (+)-FR900482. Part 2. Efficient Syntheses of the Aromatic and the Optically Active Aliphatic Fragments.

ChemInform ◽  
2010 ◽  
Vol 27 (34) ◽  
pp. no-no
Author(s):  
T. YOSHINO ◽  
Y. NAGATA ◽  
E. ITOH ◽  
M. HASHIMOTO ◽  
T. KATOH ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Optically Active

scholarly journals Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Carmen Pérez Morales ◽  
M. Mar Herrador ◽  
José F. Quílez del Moral ◽  
Alejandro F. Barrero
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Radical Cyclization ◽  
Formal Synthesis ◽  
Common Precursor ◽  
Enantiospecific Synthesis ◽  
Optically Pure

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).

A general method for the enantiospecific synthesis of optically active aliphatic sulfenyl chlorides and thiophthalimides

1990 ◽  
Vol 1 (3) ◽  
pp. 141-142 ◽  
Author(s):  
Giorgio Cevasco ◽  
Enrica Narisano ◽  
Sergio Thea
Keyword(s):  
Optically Active ◽  
Sulfenyl Chlorides ◽  
Enantiospecific Synthesis ◽  
General Method

ChemInform Abstract: Palladium-Mediated Asymmetric Synthesis of cis-3,6-Disubstituted Cyclohexenes. A Short Total Synthesis of Optically Active (+)-γ- Lycorane.

ChemInform ◽  
2010 ◽  
Vol 26 (34) ◽  
pp. no-no
Author(s):  
H. YOSHIZAKI ◽  
H. SATOH ◽  
Y. SATO ◽  
S. NUKUI ◽  
M. SHIBASAKI ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Optically Active

ChemInform Abstract: TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS, XIV. SYNTHESIS OF ESTRADIOL

1976 ◽  
Vol 7 (43) ◽  
pp. no-no
Author(s):  
U. EDER ◽  
H. GIBIAN ◽  
G. HAFFER ◽  
G. NEEF ◽  
G. SAUER ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Optically Active
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