Strategies for ansamycin antibiotics. Asymmetric synthesis of the C(3)-C(21) subunit of herbimycin A

被引：16

作者：

Martin, SF ^{[1
]}

Limberakis, C ^{[1
]}

Burgess, LE ^{[1
]}

Hartmann, M ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 12期

关键词：

ansa compounds; pyrans; alkenes; stereospecificity;

D O I：

10.1016/S0040-4020(98)01163-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of 25, which constitutes the C(3)-C(21) segment of the stereochemically complex ansa chain of herbimycin A (2) has been achieved. The approach features the furan-hydropyran transformations 7-->5 and 8-->6 and the fragment coupling of 5 and 6 to produce the trisubstituted alkene 4 with high stereoselectivity. Stereoselective addition of the aryl anion derived from 24, which possesses the novel BIPSOP protecting group for the primary amine function, to the lactol 22 then delivered 25 as the major product. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3561 / 3572

页数：12

共 72 条

[1]

[Anonymous], 1976, Org. React

[2] TOTAL SYNTHESIS OF (+)-MACBECIN-I [J].