Synthesis of the C4-C16 Polyketide Fragment of Portimines A and B

被引：6

作者：

Ding, Xiao-Bo ^{[1
]}

Aitken, Harry R. M. ^{[1
]}

Pearl, Esperanza S. ^{[1
]}

Furkert, Daniel P. ^{[1
,2
]}

Brimble, Margaret A. ^{[1
,2
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland 1010, New Zealand

[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Auckland 1010, New Zealand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 18期

关键词：

SHELLFISH POISON; SPIROLIDE-C; GYMNODIMINE; PINNATOXIN; IDENTIFICATION; DINOFLAGELLATE; SPIROIMINE; TOXINS; EFFICIENT; SEGMENT;

D O I：

10.1021/acs.joc.1c01463

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective synthesis of the C4-C16 polyketide fragment of portimines A and B is reported, enabled by our previously established method for the stereoselective synthesis of syn-alpha,alpha'-dihydroxyketones. The preparation of this advanced fragment provides insights useful for the total synthesis of portimines A and B. An asymmetric Evans aldol reaction was used to install the C10-C11 adjacent stereogenic centers before incorporation of indantrione, followed by epoxidation and epoxide opening to forge the challenging syn-alpha,alpha'-dihydroxyketone functionality.

引用

页码：12840 / 12850

页数：11

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