ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Asymmetric synthesis of machilin C and its analogue
Yamu Xia and Wei Wang
College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, 266042 China
Abstract: Full details of the asymmetric total synthesis of erythro-8-O-4′-neolignan, machilin C, and its analogue perseal A are reported. The synthesis was involved in the Sharpless dihydroxylation
reaction that occurred with excellent asymmetric induction, and the Mitsunobu reaction which occurred with inversion of the
absolute configuration from the threo to the erythro isomer. The synthesis was achieved from simple vanillin in eight to twelve steps.
Keywords: neolignans - machilin C - perseal A - asymmetric synthesis
Full paper is available at www.springerlink.com.
Chemical Papers 64 (5) 630–636 (2010)