Natural Product Total Synthesis Via Vinyl Sulfones

Fuchs, Philip L.

Abstract

T three-project synthetic program designed to fully exploit the preparative value of multiply-convergent operations utilizing vinyl sulfones is proposed. The specific natural product targets include the morphine alkaloids as well as diterpenes of the Lathrane, (Jolkinol C,D), Tigliane (Phorbol), Daphnane (12-Hydroxydaphnatoxin), and Ingenane (Ingenol) classes.

Funding Agency

• Agency: National Institute of Health (NIH)
• Institute: National Institute of General Medical Sciences (NIGMS)
• Type: Research Project (R01)
• Project #: 5R01GM032693-07
• Application #: 3281738
• Study Section: Medicinal Chemistry Study Section (MCHA)
• Project Start: 1983-12-01
• Project End: 1990-11-30
• Budget Start: 1989-12-01
• Budget End: 1990-11-30
• Support Year: 7
• Fiscal Year: 1990

Institution

• Name: Purdue University
• Type: Schools of Arts and Sciences
• DUNS #: 072051394
• City: West Lafayette
• State: IN
• Country: United States
• Zip Code: 47907

Publications

Jiang, W; Lantrip, D A; Fuchs, P L (2000) Synthesis of enantiopure termini-differentiated heptane stereotriads. Application to side chain-functionalized tetrahydrofurans of IKD-8344. Org Lett 2:2181-4

Hentemann, M; Fuchs, P L (1999) Asymmetric epoxy cyclohexenyl sulfones: readily accessible progenitors of stereo defined six-carbon arrays. Org Lett 1:355-7

Wood, K V; Rothwell, A P; Anderson, M B et al. (1990) The intramolecular migration of a trimethylsilyl group located alpha to a sulfone in substituted cyclohexyl systems. Rapid Commun Mass Spectrom 4:1-4