TOTAL SYNTHESIS OF MAREMYCINS A AND D1 USING CHIRAL AND CYCLIC NITRONE WITH (E)-3-ETHYLIDENE-1-METHYLINDOLIN-2-ONE

被引：6
作者：
Ueda, Tohru [1 ]
Inada, Mitsuhide [1 ]
Morita, Nobuyoshi [1 ]
Tamura, Osamu [1 ]
机构：
[1] Showa Pharmaceut Univ, Machida, Tokyo 1948543, Japan
来源：
HETEROCYCLES | 2015年 / 90卷 / 02期
关键词：
Maremycin A; Maremycin B; Nitrone; Cycloaddition Reaction; 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; ALLYLIC ALCOHOL; AMINO-ACIDS; DIPOLAROPHILES; DERIVATIVES; OXINDOLES; DIKETOPIPERAZINES; REGIOSELECTIVITY; CONSTRUCTION;
D O I：
10.3987/COM-14-S(K)93
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total syntheses of maremycin A (4) and maremycin D, (8) were described, featuring 1,3-dipolar cycloaddition of a chiral cyclic nitrone 15 with (E)-3-ethylidene-1-methylindolin-2-one (13). The cycloaddition was reversible, especially at high temperature in the presence of a Lewis acid or in a solvent possessing a high acceptor number. One of the cycloadducts was efficiently led to maremycin A (4) and maremycin D, (8). High optical purity of 4 was confirmed by chiral HPLC comparison with ent-4 prepared from ent-15 and 13.
引用
收藏
页码：1179 / 1195
页数：17
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