Abstract
An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.
Original language | English |
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Pages (from-to) | 5240-5242 |
Number of pages | 3 |
Journal | Tetrahedron Letters |
Volume | 57 |
Issue number | 47 |
DOIs | |
Publication status | Published - 2016 |
Keywords
- Amphidinolide
- Cytotoxic
- Macrolide
- Partial synthesis
- Polyketide
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry