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Synthesis of a Small-Molecule Library With Skeletal Diversity From Hemslecin A via the Reaction-Discovery Strategy

Synthesis of a Small-Molecule Library With Skeletal Diversity From Hemslecin A via the Reaction-Discovery Strategy

Jian Ren, Xin Shi, Xiao-Nian Li, Lai-Wei Li, Jia Su, Li-Dong Shao, Qin-Shi Zhao

Org Lett. 2016 Aug 19;18(16):3948-51.

PMID: 27486900

Abstract:

An efficient reaction tool box was developed for the synthesis of skeletally diverse and stereochemically complex templates for a small-molecule library based on the common synthon Q, which was prepared from hemslecin A in four steps. The reaction tool box comprises three acid-promoted rearrangements: semipinacol, Wagner-Meerwein, and cyclopropylmethyl cation rearrangements. More importantly, a Mn-mediated C-H oxidation was developed to achieve a high level of complexity, which provides a new entry for C-H functionalization of inert angular methyl groups in the chemistry of triterpenes. Our reaction-discovery strategy based on hemslecin A provides a basis for the inherent chemistry of triterpenes and could be applied for the further transformation of triterpenes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP58546342	Hemslecin A		58546-34-2	Price

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