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Formal Total Synthesis of (-)-Isolaurallene and Structure Determination of (+)-4-epi-Isolaurallene via

Youngjik Park¹, Hongjun Jang¹, Soo Yeon Kwak¹

¹College of Pharmacy and Research Institute of Pharmaceutical Science and Technology (RIPST), Ajou University, Suwon 16499, Korea.

Organic Letters

|March 24, 2025

Abstract:

Described herein are the formal total syntheses of (-)-isolaurallene (1) and structure determination of newly isolated (+)-4-epi-isolaurallene (2) via a highly stereodivergent intramolecular amide enolate alkylation (IAEA) strategy. Highly stereoselective constructions of α,α'-trans-THF 3 and α,α'-cis-THF 4 were accomplished by subjecting common intermediate 5 to non-chelate-controlled and chelate-controlled IAEA, respectively. The former protocol greatly improves the moderate stereoselectivity previously observed in constructing α,α'-trans-THF rings via intramolecular nitrile anion alkylation (INAA).

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