Total Synthesis of (+)–Haperforin G

(+)-Haperforin G was synthesized in 20 steps from commercially available starting materials. A Co-catalyzed intramolecular Pauson–Khand reaction was used for stereoselective construction of cyclopentanone bearing an all-carbon quaternary stereogenic center at the bridge-head position. Light-initiate...

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Published inJournal of organic chemistry Vol. 88; no. 15; pp. 10539 - 10554
Main Authors Zhang, Zhenyu, Zhang, Wei, Tang, Jun−Chen, Che, Jin−Teng, Zhang, Zhongchao, Chen, Jia−Hua, Yang, Zhen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.08.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PAUSON-KHAND REACTION
REDUCTION
ONE-POT SYNTHESIS
ALLYLIC ALCOHOLS
CONVERSION
TETRAHYDROFURAN DERIVATIVES
ALKYLATION
REARRANGED LIMONOIDS
CARBONYL-COMPOUNDS
VINYL ETHERS
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Summary:(+)-Haperforin G was synthesized in 20 steps from commercially available starting materials. A Co-catalyzed intramolecular Pauson–Khand reaction was used for stereoselective construction of cyclopentanone bearing an all-carbon quaternary stereogenic center at the bridge-head position. Light-initiated photocatalysis was used for convergent and asymmetric cross-coupling of the unstabilized C­(sp3) radical with an enone. The developed chemistry paves the way to the synthesis of structurally diverse analogs of haperforin G (6).
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00542