Abstract
The formal total synthesis of the (+)-salicylihalamides A and B is detailed, utilizing a chiral pool approach to generate the three stereogenic centers and a ring-closing metathesis (RCM) for the formation of the macrocyclic ring structure. Starting from a known glucose-derived alcohol, the formal total synthesis was achieved in an efficient 13-step protocol in 26% overall yield. It was found that substitution at the remote phenolic group significantly influenced the ratio of the E-and Z-double bond products in the RCM step. The introduction of phenol protecting groups provided E-isomers preferentially and also enhanced the rates of the RCM reactions.
Original language | English (US) |
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Pages (from-to) | 10030-10039 |
Number of pages | 10 |
Journal | Journal of Organic Chemistry |
Volume | 68 |
Issue number | 26 |
DOIs | |
State | Published - Dec 26 2003 |