Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System

The stereoselective construction of the CDEFGH ring system of lancifodilactone G is described. The key steps in this synthesis are (i) ring-closing metathesis for formation of the oxa-bridged eight-membered ring; (ii) an intramolecular Pauson–Khand reaction for construction of the sterically congest...

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Published inJournal of organic chemistry Vol. 83; no. 13; pp. 6893 - 6906
Main Authors Sun, Tian-Wen, Liu, Dong-Dong, Wang, Kuang-Yu, Tong, Bing-Qi, Xie, Jia-Xin, Jiang, Yan-Long, Li, Yong, Zhang, Bo, Liu, Yi-Fan, Wang, Yuan-Xian, Zhang, Jia-Jun, Chen, Jia-Hua, Yang, Zhen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CORE
PAUSON-KHAND REACTION
MICRANDILACTONE
GOLD CATALYSIS
NATURAL-PRODUCTS
CONSTRUCTION
EFFICIENT SYNTHESIS
ABC RING
ACTIVATED DOUBLE-BONDS
STEREOCONTROLLED SYNTHESIS
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Summary:The stereoselective construction of the CDEFGH ring system of lancifodilactone G is described. The key steps in this synthesis are (i) ring-closing metathesis for formation of the oxa-bridged eight-membered ring; (ii) an intramolecular Pauson–Khand reaction for construction of the sterically congested F ring; and (iii) sequential cross-metathesis, hydrogenation, and lactonization reactions for installation of the anomerically stabilized bis-spiro ketal fragment of lancifodilactone G.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02915