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
收藏
页码：4364 / 4373
页数：10
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