Synthesis of (-)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition-Rearrangement and Cross-electrophile Coupling

Younes Fegheh-Hassanpour, Tanzeel Arif, Herman O. Sintim, Hamad H. Al Mamari, David M. Hodgson*

*المؤلف المقابل لهذا العمل

نتاج البحث: المساهمة في مجلةمراجعة النظراء

14 اقتباسات (Scopus)

ملخص

An asymmetric synthesis of (-)-6,7-dideoxysqualestatin H5 is reported. Key features of the synthesis include the following: (1) highly diastereoselective n-alkylation of a tartrate acetonide enolate and subsequent oxidation-hydrolysis to provide an asymmetric entry to a β-hydroxy-α-ketoester motif; (2) facilitation of Rh(II)-catalyzed cyclic carbonyl ylide formation-cycloaddition by co-generation of keto and diazo functionality through ozonolysis of an unsaturated hydrazone; and (3) stereoretentive Ni-catalyzed Csp3-Csp2 cross-electrophile coupling between tricarboxylate core and unsaturated side chain to complete the natural product.

اللغة الأصليةEnglish
الصفحات (من إلى)3540-3543
عدد الصفحات4
دوريةOrganic Letters
مستوى الصوت19
رقم الإصدار13
المعرِّفات الرقمية للأشياء
حالة النشرPublished - يوليو 7 2017

ASJC Scopus subject areas

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بصمة

أدرس بدقة موضوعات البحث “Synthesis of (-)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition-Rearrangement and Cross-electrophile Coupling'. فهما يشكلان معًا بصمة فريدة.

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