Abstract
The total synthesis of cytotoxic marine phosphomacrolides, (−)-enigmazole A and (−)-15-O-methylenigmazole A, is described in detail. The 2,6-cis-substituted tetrahydropyran ring was efficiently elaborated by using a tandem olefin cross-metathesis/intramolecular oxa-Michael addition reaction. The 18-membered macrolactone skeleton was forged via a Au-catalyzed propargylic benzoate rearrangement/macrocyclic ring-closing metathesis sequence. Late-stage diversification of a common intermediate enabled unified total synthesis of (−)-enigmazole A and (−)-15-O-methylenigmazole A.
Original language | English |
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Pages (from-to) | 3494-3502 |
Number of pages | 9 |
Journal | Chemistry - An Asian Journal |
Volume | 15 |
Issue number | 21 |
DOIs | |
Publication status | Published - 2020 Nov 2 |
Externally published | Yes |
Keywords
- gold-catalyzed reaction
- macrocycles
- natural products
- tandem reaction
- tetrahydropyrans
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry