Total synthesis achieves spiroapplanatumine G via enantioselective Diels–Alder reaction, indicating its significance in synthetic chemistry.
Spiroapplanatumine G (7) is a spiro-meroterpenoid characterized by an unusual 6/5/7 tricyclic spirobenzofuran-3-one core. The first enantioselective total synthesis of spiroapplanatumine G (7) is reported, featuring a key enantioselective Diels–Alder reaction between an aurone ester and a silyloxydiene to assemble the spirobenzofuranone core. This strategic Diels–Alder transformation advantageously establishes the two contiguous stereogenic centers in a single step. Subsequent cyclopropanation/FeCl3-mediated oxidative ring expansion affords the desired tricyclic framework.
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Lin et al. (2025) studied this question.
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