Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans

Mingyi Wang; Anxin Wu; Xinfu Pan; Hongfang Yang

doi:10.1021/jo011077o

Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans

J Org Chem. 2002 Jul 26;67(15):5405-7. doi: 10.1021/jo011077o.

Authors

Mingyi Wang¹, Anxin Wu, Xinfu Pan, Hongfang Yang

Affiliation

¹ Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.

PMID: 12126439
DOI: 10.1021/jo011077o

Abstract

The first total syntheses of the racemates of naturally occurring macrophyllin-type bicyclo[3.2.1]octanoid neolignans, kadsurenin C 3 and kadsurenin L 4, were accomplished starting from vanillin and resorcinol. The acid-catalyzed rearrangement of hydrobenzofuranoid neolignans into bicyclo[3.2.1]octanoid neolignans was used as the key step.

Publication types

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

MeSH terms

Benzaldehydes / chemistry
Bridged Bicyclo Compounds / chemical synthesis*
Catalysis
Cyclooctanes
Drugs, Chinese Herbal / chemistry*
Lignans / chemical synthesis*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Resorcinols / chemistry
Stereoisomerism

Substances

Benzaldehydes
Bridged Bicyclo Compounds
Cyclooctanes
Drugs, Chinese Herbal
Lignans
Resorcinols
kadsurenin C
kadsurenin L
vanillin
resorcinol