Brefeldin Corey synthesis

Methylthiomethyl ethers are comparable in stability to alkoxymethyl ethers towards strongly basic conditions or mild acid. For example, methylthiomethyl ethers survive aqueous acetic acid under conditions that hydrolyse TBS ethers, dioxolanes or tetrahydropyranyl protectors. They can be removed under rather specific and mild conditions that do not affect most acetal-type protectors such as MEM. MOM. etc. (see above). The presence of the sulfur makes this group liable to oxidation by strong oxidants such as peracids. Cr(VI), and N-bromo-succinimide, and it will poison Pd catalysts. The methylthiomethyl group was First introduced by Corey and co-workers586 and its virtues exploited by them in a synthesis of the antibiotics Erythronolide587 588 and Brefeldin.589... 

Corey et al have reported some modifications to their previously published synthesis of brefeldin A (111), and a group led by Crabbe has developed an alternative approach to the key a>-hydroxy-acid used in Corey s synthesis. Another synthesis of (111) has also been recorded. " ... 

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