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Stereoselective Total Synthesis of (+/-)-Trichodiene: Biogenetic Precursor of the Trichothecane Sesquiterpenoids
Two approaches to the total synthesis of (+/-)-trichodiene (1) are reported from cis-fused lactone 10.Sequential alkylation of lactone 10 was observed to be highly stereoselective as established by the construction of diastereomeric lactone esters 12 and 14.Lactone ester 12 was utilized to prepare (+/-)-trichodiene (1) with a high degree of regioselectivity.All attempts to synthesize (+/-)-bazzanene (2), the diastereomer of (+/-)-trichodiene (1), from lactone 13 were found to be unsuccessful in the last stage of the synthetic scheme.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics