Formal total synthesis of neopeltolide |
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Authors: | Vintonyak Viktor V Maier Martin E |
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Affiliation: | Institut für Organische Chemie, Universit?t Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany. |
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Abstract: | A concise synthesis of the core structure of the macrolide neopeltolide was developed featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leighton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchi macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%. |
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