Total synthesis of (+/-)-pallavicinin and (+/-)-neopallavicinin

Xiao-Shui Peng; Henry N C Wong

doi:10.1002/asia.200600061

Total synthesis of (+/-)-pallavicinin and (+/-)-neopallavicinin

Chem Asian J. 2006 Jul 17;1(1-2):111-20. doi: 10.1002/asia.200600061.

Authors

Xiao-Shui Peng¹, Henry N C Wong

Affiliation

¹ Department of Chemistry, Centre of Novel Functional Molecules, Institute of Chinese Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.

PMID: 17441045
DOI: 10.1002/asia.200600061

Abstract

Through a biomimetic pathway, (+/-)-pallavicinin and (+/-)-neopallavicinin were synthesized from (+/-)-Wieland-Miescher ketone via Grob fragmentation, intramolecular aldol cyclization, and intramolecular Michael reaction. The synthesis was stereocontrolled efficiently and followed the stereochemistry of the Wieland-Miescher ketone, and could provide opportunities for access to analogues of pallavicinin, neopallavicinin, and other related bioactive diterpenoids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Circular Dichroism
Diterpenes / chemistry
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Magnetic Resonance Spectroscopy
Stereoisomerism

Substances

Diterpenes
Heterocyclic Compounds, 4 or More Rings
pallavicinin