Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor

被引：71

作者：

Hayashi, Y ^{[1
]}

Shoji, M

Yamaguchi, J

Sato, K

Yamaguchi, S

Mukaiyama, T

Sakai, K

Asami, Y

Kakeya, H

Osada, H

机构：

[1] Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan

[2] Sci Univ Tokyo, Dept Appl Chem, Fac Sci, Shinjuku Ku, Tokyo 1628601, Japan

[3] RIKEN, Antibiot Lab, Wako, Saitama 3510198, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 41期

关键词：

D O I：

10.1021/ja0276826

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2·OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized γ-lactam moiety without protection of tert-alcohol and amide functionalities. Copyright © 2002 American Chemical Society.

引用

页码：12078 / 12079

页数：2

共 31 条

[1]

ALLEN CFH, 1973, ORG SYNTH, V3, P731

[2] SYNERAZOL, A NEW ANTIFUNGAL ANTIBIOTIC [J].

ANDO, O ;

SATAKE, H ;

NAKAJIMA, M ;

SATO, A ;

NAKAMURA, T ;

KINOSHITA, T ;

FURUYA, K ;

HANEISHI, T .

JOURNAL OF ANTIBIOTICS, 1991, 44 (04) :382-389

[3] Azaspirene:: A novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartotya sp. [J].

Asami, Y ;

Kakeya, H ;

Onose, R ;

Yoshida, A ;

Matsuzaki, H ;

Osada, H .

ORGANIC LETTERS, 2002, 4 (17) :2845-2848

[4] ISOLATION AND STRUCTURE OF PSEUROTIN-A, A MICROBIAL METABOLITE OF PSEUDEUROTIUM-OVALIS STOLK WITH AN UNUSUAL HETEROSPIROCYCLIC SYSTEM [J].

BLOCH, P ;

TAMM, C .

HELVETICA CHIMICA ACTA, 1981, 64 (01) :304-315

[5]

BLOCH P, 1976, HELV CHIM ACTA, V59, P133, DOI 10.1002/hlca.19760590114

[6] PSEUROTIN-B, PSEUROTIN-C, PSEUROTIN-D, AND PSEUROTIN-E FURTHER NEW METABOLITIES OF PSEUDEUROTIUM-OVALIS STOLK [J].

BREITENSTEIN, W ;

CHEXAL, KK ;

MOHR, P ;

TAMM, C .

HELVETICA CHIMICA ACTA, 1981, 64 (02) :379-388

[7] Synthesis of phenethylenamides and their radical cyclization to 3-benzazepines. [J].

Cid, MM ;

Domínguez, D ;

Castedo, L ;

Vázquez-López, EM .

TETRAHEDRON, 1999, 55 (17) :5599-5610

[8] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[9] 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

[10] SYNTHETIC STUDIES DIRECTED TOWARD THE PSEUROTINS .1. SYNTHESIS OF RELATED FURAN-3(2H)-ONES [J].

DOLDER, M ;

XIE, S ;

TAMM, C .

HELVETICA CHIMICA ACTA, 1990, 73 (01) :63-68

← 1 2 3 4 →