A Formal Synthesis of Herboxidiene/GEX1A

A formal synthesis of herboxidiene/GEX 1A is described. This approach demonstrates successful application of the Prins cyclization for the construction of the tetrahydropyran core of the target molecule. The chirality of the side chain has been established through the Sharpless asymmetric dihydroxyl...

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Veröffentlicht in:European journal of organic chemistry 2014-07, Vol.2014 (20), p.4389-4397
Hauptverfasser: Yadav, Jhillu S., Reddy, G. Madhusudhan, Anjum, S. Rehana, Reddy, B. V. Subba
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Sprache:eng
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Zusammenfassung:A formal synthesis of herboxidiene/GEX 1A is described. This approach demonstrates successful application of the Prins cyclization for the construction of the tetrahydropyran core of the target molecule. The chirality of the side chain has been established through the Sharpless asymmetric dihydroxylation and Evan's alkylation. The olefin cross‐metathesis was applied to couple both key fragments. We present a convergent and stereoselective synthesis of GEX 1A/Herboxidiene in 22 steps. An enantioselective crotylation and Prins cyclization builds the tetrahydropyran core. Sharpless asymmetric dihydroxylation and Evans' alkylation reactions establish the key chiral centers. Finally, olefin cross‐metathesis assembles the functionalized tetrahydropyran and polyoxygenated side chain.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402235