Systematic synthesis of bis-THF ring cores in annonaceous acetogenins

被引：37

作者：

Maezaki, N ^{[1
]}

Kojima, N ^{[1
]}

Tominaga, H ^{[1
]}

Yanai, M ^{[1
]}

Tanaka, T ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 09期

关键词：

D O I：

10.1021/ol034131r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic Systematic synthesis of bis-THF ring cores, synthetic intermediates of adjacent bis-THF annonaceous acetogenins, has been achieved by asymmetric alkynylation and subsequent stereodivergent THF ring formation. The asymmetric alkynylation of alpha-tetrahydrofuranic aldehyde with (S)-3-butyne-1,2-diol derivatives gave good yields of erythro- and threo-adducts with very high diastereoselectivity. These adducts were converted into four types of bis-THF cores via two kinds of one-pot THF ring formation.

引用

页码：1411 / 1414

页数：4

共 37 条

[1] Annonaceous acetogenins: Recent progress
Alali, FQ
Liu, XX
McLaughlin, JL
[J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03): : 504 - 540
[2] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
Anand, NK
Carreira, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) : 9687 - 9688
[3] Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes
Boyall, D
López, F
Sasaki, H
Frantz, D
Carreira, EM
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4233 - 4236
[4] Bruns R, 2000, CHEM-EUR J, V6, P1337, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1337::AID-CHEM1337>3.0.CO
[5] 2-K
[6] Casiraghi G., 1998, CHEMTRACTS ORG CHEM, V11, P803
[7] Cave A, 1997, Fortschr Chem Org Naturst, V70, P81
[8] Direct synthesis of substituted tetrahydrofurans via regioselective dehydrative polyol cyclization cascades
Dounay, AB
Florence, GJ
Saito, A
Forsyth, CJ
[J]. TETRAHEDRON, 2002, 58 (10) : 1865 - 1874
[9] Synthetic studies toward the C5-C20 domain of the azaspiracids
Dounay, AB
Forsyth, CJ
[J]. ORGANIC LETTERS, 2001, 3 (07) : 975 - 978
[10] Asymmetric synthesis of γ-hydroxy α,β-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes
El-Sayed, E
Anand, NK
Carreira, EM
[J]. ORGANIC LETTERS, 2001, 3 (19) : 3017 - 3020

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