Add time:08/24/2019         Source:sciencedirect.com

vinigrol (cas 111025-83-3) is diterpene isolated from a fungus strain Virgaria nigra F-5408. Its tricyclic core comprises a cis-fused [4.4.0] system surmounted by a four-carbon bridge at C1 and C5 and features eight contiguous stereocenters. Biological testing of vinigrol has revealed a number of interesting properties. Not surprisingly, the remarkable biological activities of vinigrol, combined with its unique and synthetically challenging structure, have caused considerable attention from the synthetic community. Herein, we reported all of our approaches toward the synthesis of this complex natural product over 9 years. In 2011, we reported the first formal synthesis of vinigrol in 24 steps from commercially available starting materials. A unique strategic feature of our synthesis comprises the construction of the vinigrol carbocyclic core in only 12 steps through a sequence involving a stereocontrolled Claisen rearrangement and an intramolecular Diels–Alder reaction as key steps. In addition, we took advantage of the compact nature of the vinigrol core to install the other functionalities in a stereoselective manner.

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