Synthesis of bistramide A and analogues, Part 1: Stereoselective access to normethyl tetrahydropyran subunit

被引：16

作者：

Hiebel, Marie-Aude ^{[1
]}

Pelotier, Beatrice ^{[1
]}

Lhoste, Paul ^{[1
]}

Piva, Olivier ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, ICBMS, UMR 5246, F-69622 Villeurbanne, France

来源：

SYNLETT | 2008年 / 08期

关键词：

bistramide A; normethyl; Sharpless epoxidation; cross-metathesis reaction; intramolecular oxa-Michael reaction;

D O I：

10.1055/s-2008-1072714

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of normethyl C1-C13 fragment of bistramide A is described. The key steps involve an asymmetric Sharpless epoxidation, a cross-metathesis reaction and an intramolecular oxa-Michael reaction. The trans-2,6-disubstituted tetrahydropyran subunit has been synthesized in an overall yield of 7% with 96% ee. The cis isomer was prepared by a similar pathway with the same efficiency and enantioselectivity.

引用

页码：1202 / 1204

页数：3

共 30 条

[1] Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double bond geometry in controlling the diastereoselectivity of cyclisations leading to 2,6-disubstituted tetrahydropyrans and piperidines [J].

Banwell, MG ;

Bui, CT ;

Pham, HTT ;

Simpson, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10) :967-969

[2] Model studies towards the bistramide D tetrahydropyran [J].

Bates, Roderick W. ;

Palani, Kalpana .

TETRAHEDRON LETTERS, 2008, 49 (17) :2832-2834

[3] BISTRAMIDE-A, BISTRAMIDE-B, BISTRAMIDE-C, BISTRAMIE-D, AND BISTRAMIDE-K - A NEW CLASS OF BIOACTIVE CYCLIC POLYETHERS FROM LISSOCLINUM-BISTRATUM [J].

BIARD, JF ;

ROUSSAKIS, C ;

KORNPROBST, JM ;

GOUIFFESBARBIN, D ;

VERBIST, JF ;

COTELLE, P ;

FOSTER, MP ;

IRELAND, CM ;

DEBITUS, C .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (10) :1336-1345

[4] A general model for selectivity in olefin cross metathesis [J].

Chatterjee, AK ;

Choi, TL ;

Sanders, DP ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370

[5] Enantioselective total synthesis of bistramide A [J].

Crimmins, MT ;

DeBaillie, AC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4936-4937

[6] Molecular simplification in bioactive molecules:: Formal synthesis of (+)-muconin [J].

Crisóstomo, FRP ;

Carrillo, R ;

León, LG ;

Martín, T ;

Padrón, JM ;

Martín, VS .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2339-2345

[7] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[8] A simple asymmetric synthesis of cis-2,6-disubstituted tetrahydropyran acetic acid derivatives [J].

Edmunds, AJF ;

Trueb, W .

TETRAHEDRON LETTERS, 1997, 38 (06) :1009-1012

[9] Stereoselective construction of cyclic ethers using a tandem two-component etherification: Elucidation of the role of bismuth tribromide [J].

Evans, PA ;

Cui, J ;

Gharpure, SJ ;

Hinkle, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11456-11457

[10] REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES [J].

FINAN, JM ;

KISHI, Y .

TETRAHEDRON LETTERS, 1982, 23 (27) :2719-2722

← 1 2 3 →