Total synthesis of natural (+)-FR900482 .3. Completion of the synthesis

被引：30

作者：

Katoh, T ^{[1
]}

Yoshino, T ^{[1
]}

Nagata, Y ^{[1
]}

Nakatani, S ^{[1
]}

Terashima, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 20期

关键词：

D O I：

10.1016/0040-4039(96)00595-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title synthesis was accomplished by featuring (i) coupling of the aromatic fragment 2 with the optically active aliphatic fragment 3 to install the requisite carbon unit (2+3-->4); (ii) intramolecular aldol reaction of the highly functionalized dialdehyde IO to produce the desired eight-membered ring system 11 (10-->11); (iii) epimerization of the C-7 position of hydroxy ketone 14 to obtain the correct stereochemistry (14-->15); (iv) internal hemiacetal formation of hydroxylamino ketone 23 in situ generated from ketone 22 to construct the requisite tetracyclic ring system 24 (23-->24) as key steps. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：3479 / 3482

页数：4

共 13 条

[1] 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].