Abstract
(Matrix Presented) This Letter describes a concise, diastereoselective synthesis of the tricyclic carbon framework of the guanacastepene family of natural products. An intermolecular Diels-Alder reaction established a remote stereochemical relationship and facilitated a synthesis of allylic acetate 3, which was subsequently joined with vinylstananne 9 via a Stille coupling. An intramolecular [2 + 2] photocycloaddition then afforded complex cyclobutyl ketone 19, which underwent a stereoelectronically controlled fragmentation to the guanacastepene architecture on treatment with samarium diiodide.
Original language | English (US) |
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Pages (from-to) | 2063-2066 |
Number of pages | 4 |
Journal | Organic letters |
Volume | 4 |
Issue number | 12 |
DOIs | |
State | Published - Jun 13 2002 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry