Towards the total synthesis of calyculin C: preparation of the C9-C25 spiroketal-dipropionate unit

被引：5

作者：

Habrant, Damien ^{[1
]}

Koskinen, Ari M. P. ^{[1
]}

机构：

[1] Aalto Univ, Dept Chem, Organ Chem Lab, Sch Sci & Technol, FI-00076 Aalto, Finland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 19期

关键词：

SPONGE DISCODERMIA-CALYX; THREONINE PROTEIN PHOSPHATASES; BIOACTIVE MARINE METABOLITES; NATURAL-PRODUCTS; ASYMMETRIC-SYNTHESIS; FRAGMENT; INHIBITORS; ALDEHYDES; SUBUNIT; ACID;

D O I：

10.1039/c0ob00092b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of the C-9-C-25 spiroketal fragment of calyculin C is described. Key steps include two crotylation reactions using successively Brown's reagent and (Z)-crotyltrifluorosilane for the formation of the anti, anti, anti stereotetrad, ynone formation by a Pd-catalyzed coupling of a thiol ester with a terminal alkyne and a double intramolecular hetero-Michael addition for the stereoselective construction of the spiroketal framework.

引用

页码：4364 / 4373

页数：10

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