Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization

Being different from 2,6-cis-tetrahydropyrans (2,6-cis-THPs), the corresponding 2,6-trans-THPs are thermodynamically less stable and more challenging to construct. The fact that there are many natural products and/or bioactive molecules containing this 2,6-trans-THP subunit has led to the development of many efficient synthetic approaches to access 2,6-trans-THPs. This review summarizes various synthetic methods reported for this structural motif and/or related applications in the total synthesis of natural products.1 Introduction2 Nucleophilic Addition to an Oxocarbenium Ion (Strategy A)3 Intramolecular Oxa-Michael Addition (Strategy B)4 Intermolecular Michael Addition to Dihydropyranones (Strategy A)5 The Heck–Matsuda (Strategy A) Reaction and Oxa-Heck Cyclization (Strategy B)6 Intramolecular SN2 Substitution and Epoxide Opening (Strategy B)7 Miscellaneous Methods8 Conclusion and Outlook

Download Full-text

Total Synthesis of (−)-Galanthamine and (−)-Lycoramine via Catalytic Asymmetric Hydrogenation and Intramolecular Reductive Heck Cyclization

Organic Letters ◽

10.1021/ol300913g ◽

2012 ◽

Vol 14 (11) ◽

pp. 2714-2717 ◽

Cited By ~ 82

Author(s):

Ji-Qiang Chen ◽

Jian-Hua Xie ◽

Deng-Hui Bao ◽

Sheng Liu ◽

Qi-Lin Zhou

Keyword(s):

Total Synthesis ◽

Asymmetric Hydrogenation ◽

Heck Cyclization ◽

Catalytic Asymmetric ◽

Catalytic Asymmetric Hydrogenation

Download Full-text

Total Synthesis of (±)-Cytisine via the Intramolecular Heck Cyclization of ActivatedN-Alkyl Glutarimides

Organic Letters ◽

10.1021/ol006765t ◽

2000 ◽

Vol 2 (26) ◽

pp. 4205-4208 ◽

Cited By ~ 52

Author(s):

Jotham W. Coe

Keyword(s):

Total Synthesis ◽

Heck Cyclization

Download Full-text

ChemInform Abstract: Total Synthesis of (.+-.)-Cytisine via the Intramolecular Heck Cyclization of Activated N-Alkyl Glutarimides.

ChemInform ◽

10.1002/chin.200116217 ◽

2001 ◽

Vol 32 (16) ◽

pp. no-no

Author(s):

Jotham W. Coe

Keyword(s):

Total Synthesis ◽

Heck Cyclization

Download Full-text

Concise Total Synthesis of Antiarrhythmic Drug Dronedarone via a Conjugate Addition Followed Intramolecular Heck Cyclization

Journal of Heterocyclic Chemistry ◽

10.1002/jhet.4316 ◽

2021 ◽

Author(s):

Sai Reddy Doda ◽

Madhu Madasu ◽

Prem Kumar Begari ◽

Krishna Rao Dasari ◽

Gangadhar Thalari ◽

...

Keyword(s):

Total Synthesis ◽

Antiarrhythmic Drug ◽

Conjugate Addition ◽

Heck Cyclization

Download Full-text

Intramolecular Heck cyclization to the galanthamine-type alkaloids: total synthesis of (±)-lycoramine

Tetrahedron ◽

10.1016/j.tet.2004.09.044 ◽

2004 ◽

Vol 60 (50) ◽

pp. 11655-11660 ◽

Cited By ~ 20

Author(s):

Pi-Hui Liang ◽

Jing-Ping Liu ◽

Ling-Wei Hsin ◽

Chen-Yu Cheng

Keyword(s):

Total Synthesis ◽

Heck Cyclization

Download Full-text

Chemoenzymatic Total Synthesis of (+)-Oxycodone from Phenethyl Acetate

Synthesis ◽

10.1055/s-0037-1611335 ◽

2018 ◽

Vol 51 (01) ◽

pp. 225-232 ◽

Cited By ~ 9

Author(s):

Mary Ann Endoma-Arias ◽

Mariia Makarova ◽

Helen Dela Paz ◽

Tomas Hudlicky

Keyword(s):

Total Synthesis ◽

Spectral Data ◽

Recombinant Strain ◽

Radical Cyclization ◽

Quaternary Carbon ◽

Heck Cyclization ◽

The Absolute ◽

Phenethyl Acetate ◽

New Compounds ◽

Absolute Stereochemistry

The stereoselective total synthesis of unnatural (+)-oxycodone from phenethyl acetate is described. Absolute stereochemistry was established via microbial dihydroxylation of phenethyl acetate with the recombinant strain JM109 (pDTG601A) to the corresponding cis-cyclohexadienediol whose configuration provides for the absolute stereochemistry of the ring C of (+)-oxycodone. Intramolecular Heck cyclization was employed to establish the quaternary carbon at C-13, along with the dibenzodihydrofuran functionality. The C-14 hydroxyl was installed via SmI2-mediated radical cyclization. The synthesis of (+)-oxycodone was completed in a total of 13 steps and an overall yield of 1.5%. Experimental and spectral data are provided for all new compounds.

Download Full-text