Enantioselective Syntheses of Pachastrissamine and Jaspine AviaHydroxylactonization of a Chiral Epoxy Ester | Zendy

Hiroyuki Urano | Zendy; Masaru Enomoto | Zendy; Shigefumi Kuwahara | Zendy

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Enantioselective Syntheses of Pachastrissamine and Jaspine AviaHydroxylactonization of a Chiral Epoxy Ester

Author(s) -

Hiroyuki Urano,

Masaru Enomoto,

Shigefumi Kuwahara

Publication year - 2010

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.90670

Subject(s) - enantioselective synthesis , epoxide , epoxy , chirality (physics) , aldehyde , chemistry , ring (chemistry) , yield (engineering) , intramolecular force , stereochemistry , oxazolidine , organic chemistry , catalysis , materials science , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , metallurgy , quark

A new enantioselective total synthesis of pachastrissamine (jaspine B) was achieved from a known alpha,beta-unsaturated aldehyde by utilizing Córdova's asymmetric epoxidation as the chirality-inducing step. The 2,3-cis stereochemistry of pachastrissamine was established via intramolecular epoxide ring opening of a gamma,delta-epoxy-alpha,beta-unsaturated ester intermediate coupled with oxy-Michael cyclization. Treatment of pachastrissamine with tetrahydro-2-furanol under acidic conditions led to smooth oxazolidine ring formation, furnishing jaspine A in a high yield.

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