CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .33. STEREOSELECTIVE SYNTHESIS OF POLYETHER ANTIBIOTICS, LASALOCID-A AND ISOLASALOCID-A, VIA A CHELATION-CONTROLLED FORMATION OF TETRAHYDROFURAN RINGS UNDER THERMODYNAMIC CONDITIONS

被引：8

作者：

NODA, I ^{[1
]}

HORITA, K ^{[1
]}

OIKAWA, Y ^{[1
]}

YONEMITSU, O ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)98022-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The B-rings (2,5-trans-tetrahydrofurans) of lasalocid A (6) and isolasalocid A (7) were stereoselectively constructed from the corresponding p-methoxyphenylallyl alcohols (13a, 13b) by treatment with ZnBr2 to give C13-C24 fragments (14a, 14b) via a new chelation-controlled cyclization under thermodynamic conditions. After their conversion into lasalocid ketone (19) and BOM-isolasalocid ketone (20), coupling with the C1-C11 aldehyde (22) completed the synthesis of 6 and 7, respectively. © 1990.

引用

页码：6035 / 6038

页数：4

共 29 条

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