Efficient construction of 8-membered ring framework of vinigrol through SmI2-induced coupling cyclization

Article abstract of DOI:10.1016/S0040-4020(99)00885-6

The 8-membered ring framework of vinigrol, a unique tricyclic diterpene isolated as a novel antihypertensive compound from a culture of Virgaria nigra, was efficiently synthesized employing an SmI₂-induced intramolecular coupling. It is particularly noteworthy that the 8-membered carbocycle was cyclized in quantitative yields under non-high-dilution conditions.