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Collective Biomimetic Synthesis of Myrcaulones A and C and Myrcauones B-D
Zi-Jian Peng1,2, Zhi-Zhang Duan1,2, Xiao-Xia Chen1,2
1State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou 510632, People's Republic of China.
Abstract:
We report the first collective biomimetic synthesis of noncanonical phloroglucinol derivatives myrcaulones A (1) and C (3), featuring a unique ring-contracted phloroglucinol skeleton, along with three biosynthetically related canonical phloroglucinol derivatives myrcauones B-D (4-6). These compounds were synthesized in only 6-9 steps, starting from the commercially available 3,4,5-trimethoxyphenol. Key features of the synthetic strategy include a hetero-Diels-Alder reaction to construct the canonical phloroglucinol framework and an α-ketol rearrangement-driven ring contraction reaction to form the noncanonical phloroglucinol skeleton.
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