Improved Synthesis of Castasterone and Brassinolide†
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Tsuyoshi Watanabe, Suguru Takatsuto, Shozo Fujioka and Akira Sakurai
Abstract
Castasterone 1 is synthesized in 32% overall yield in eight steps from the known (20S)-6,6-ethylenedioxy-20-formyl-3α,5-cyclo-5α-pregnane 4.
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