Abstract
A concise, enantiospecific synthesis of the phospholipase C inhibitor (-)-hispidospermidin (1) has been achieved by approximating the architecture of a reactive intermediate that may lie on the biosynthetic pathway leading to this natural product. Two compounds derived from (R)-(+)-pulegone were joined by a highly diastereoselective carbonyl addition. A proximity-facilitated, acid-induced bicyclization of spiro[4.5]deca-1,7-diene 29 gave rise to the tetracyclic framework of 1 and was the key transformation in this synthesis.
Original language | English (US) |
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Pages (from-to) | 6921-6932 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 59 |
Issue number | 35 |
DOIs | |
State | Published - Aug 25 2003 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Keywords
- Biomimetic synthesis
- Hispidospermidin
- Proximity
- π-cyclization