10‐Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)‐Dragmacidin D |
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| Authors: | Jeffrey J Jackson Dr Hiroyuki Kobayashi Sophia D Steffens Prof Dr Armen Zakarian |
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| Affiliation: | 1. Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106‐9510 (USA);2. Daiichi Sankyo Co., LTD, 1‐2‐58, Hiromachi, Shinagawa‐ku, Tokyo 140‐8710 (Japan) |
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| Abstract: | The asymmetric synthesis of dragmacidin D ( 1 ) was completed in 10 steps. Its sole stereocenter was set by using direct asymmetric alkylation enabled by a C2‐symmetric tetramine and lithium N‐(trimethylsilyl)‐tert‐butylamide as the enolization reagent. A central Larock indole synthesis was employed in a convergent assembly of the heterocyclic subunits. The stereochemical evidence from this work strongly supports the predicted S configuration at the 6′′′ position, which is consistent with other members of the dragmacidin family of natural products. |
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| Keywords: | asymmetric synthesis dragmacidin heterocycles indoles total synthesis |
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