Chemical Communications

Enantiospecific synthesis of (+)-and (–)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine

M Nambu, JD White

Index: Nambu, Mitch; White, James D. Chemical Communications, 1996 , # 14 p. 1619 - 1620

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Citation Number: 7

Abstract

Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-α and AD-mix- β, followed by saponification, gives (–)-and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.

Completely Stereocontrolled Aldol Reaction of Chiral β-Amino Acids

[Beddow, James E.; Davies, Stephen G.; Ling, Kenneth B.; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Thomson, James E. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 17 p. 2812 - 2825]

Reactivity of ambident anions: Hardness of alkyl groups and symbiotic effect in alkylation of ambident anions

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Enantiospecific synthesis of (+)-and (–)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine

Abstract

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