Abstract
(Chemical Equation Presented) Nitroalkene (E)-1 has been synthesized to test the feasibility of an intramolecular [4 + 2] cycloaddition in a planned synthesis of daphnilactone B. This nitro olefin contains two unique structural features, a nitromethylene lactone and a pendant diene, that combine under the action of SnCl4 in a highly selective fashion to afford nitronates 2a and 2b. These products represent the correct relationship for the vicinal quaternary stereogenic centers in the core of daphnilactone B.
Original language | English (US) |
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Pages (from-to) | 5617-5620 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 7 |
Issue number | 25 |
DOIs | |
State | Published - Dec 8 2005 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry