Construction of Iterative Tetrahydrofuran Ring Units and Total Synthesis of (+)-Goniocin

被引：12

作者：

Suzuki, Ai ^{[1
]}

Sasaki, Mai ^{[1
]}

Nakagishi, Tetsuya ^{[1
]}

Ueda, Tsuyoshi ^{[1
]}

Hoshiya, Naoyuki ^{[1
]}

Uenishi, Jun'ichi ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Kyoto 6078412, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 09期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; ANNONACEOUS ACETOGENINS; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE POLYCYCLIZATIONS; GONIOTHALAMUS-GIGANTEUS; ORGANOMETALLIC REAGENTS; EFFICIENT SYNTHESIS; BROWN ALGA; THF; (6S,7S,9R,10R)-6,9-EPOXYNONADEC-18-ENE-7,10-DIOL;

D O I：

10.1021/acs.orglett.6b00877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C-22-C-10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly.

引用

页码：2248 / 2251

页数：4

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