Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol

被引：4

作者：

Doda, Sai Reddy ^{[1
]}

Raghavendar, Avula ^{[2
]}

Haridasyam, Sharath Babu ^{[2
]}

Putta, Chandra Shekar ^{[3
]}

Rao, Bhattu Kanakadurga ^{[3
]}

Kadari, Sudhakar ^{[3
]}

机构：

[1] CSIR IICT, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India

[2] GITAM Univ, Dept Chem, Hyderabad Campus, Patancheru Mandal 502329, Telangana, India

[3] Osmania Univ, Dept Chem, Hyderabad 500007, Telangana, India

来源：

HETEROCYCLIC COMMUNICATIONS | 2019年 / 25卷 / 01期

关键词：

Macrolactonisation; Natural products; Asymmetric synthesis; Heck cross coupling; C-C bond formation; NATURAL-PRODUCTS; STRUCTURE REVISION; RUGULACTONE; GENES;

D O I：

10.1515/hc-2019-0015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, short and, a convenient asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol (2) and zeaenol (1) have been achieved in 7 and 9 linear steps with the high overall yield of 32% and 21% respectively, from the known intermediate 13. Mitsunobu inversion, De Brabander's protocol for macrolactonisation, Heck cross-coupling, diastereoselective alkyne aldehyde coupling and Ohira-Bestmann alkynylation are the key reactions.

引用

页码：78 / 84

页数：7

共 23 条

[21] Large-Scale Asymmetric Synthesis of the 3,6,7,8-Tetrahydrochromeno[7,8-d]imidazole BYK 405879: A Promising Candidate for the Treatment of Acid-Related Diseases
Palmer, Andreas M.
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ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (06) : 1170 - 1182
[22] OLIVANIC ACID ANALOGS .1. TOTAL SYNTHESIS OF THE 7-OXO-1-AZABICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLATE SYSTEM AND SOME RELATED BETA-LACTAMS
BATESON, JH
BAXTER, AJG
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (12): : 3242 - 3249
[23] On the structure of passifloricin A:: Asymmetric synthesis of the δ-lactones of (2Z,5S,7R,9S,11S)- and (2Z,5R,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid
García-Fortanet, J
Murga, J
Carda, M
Marco, JA
ORGANIC LETTERS, 2003, 5 (09) : 1447 - 1449

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