doi: 10.1021/ol017261d.
Synthesis of the core structure of apicularen a by transannular cyclization
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- PMID: 11843612
- DOI: 10.1021/ol017261d
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Synthesis of the core structure of apicularen a by transannular cyclization
Org Lett.
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Abstract
[reaction: see text] An approach to the macrocyclic core of apicularen A is described. Thus, cross-coupling of the aryl triflate 7 with the vinylstannane 19 provided the styrene 20. Deprotection led to the dihydroxy acid 22. Through a size-selective macrolactonization, the 12-membered macrolactone 23 was obtained. Treatment of 24 with N-phenyl selenophthalimide gave the desired trans-pyran 24. This approach might parallel the biosynthetic pathway.
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