Synthesis of (+/-)-hamigeran B, (-)-hamigeran B, and (+/-)-1-epi-hamigeran B: use of bulky silyl groups to protect a benzylic carbon-oxygen bond from hydrogenolysis.

Abstract

Enone 42 was converted into diene 56, which was then subjected to hydrogenation. Use of the tert-butyldimethylsiloxy groups enforces facial selectivity and protects the C(5) oxygen from hydrogenolysis. The resulting product (55) is easily converted into hamigeran B (1), a marine natural product with powerful activity against herpes and polio viruses. Optically pure enone 73 was made by use of a Meyers' auxiliary and converted into (-)-hamigeran B with the natural absolute configuration.

• Authors: Derrick L J Clive, Jian Wang
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 69 Issue 8 Pg. 2773-84 (Apr 16 2004) ISSN: 0022-3263 [Print] United States
• PMID: 15074927 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Benzyl Compounds
• Naphthoquinones
• hamigeran B
• Carbon
• Oxygen
• Silicon

Topics

• Animals
• Benzyl Compounds (chemistry)
• Carbon (chemistry)
• Cyclization
• Hydrogenation
• Molecular Structure
• Naphthoquinones (chemical synthesis)
• Oxygen (chemistry)
• Porifera (chemistry)
• Silicon (chemistry)
• Stereoisomerism