Total synthesis of (+)-dibromophakellin.
Two members of a family of pyrrole-imidazole marine alkaloids, (+)-dibromophakellin and the nonnatural congener (+)-phakellin, were synthesized enantioselectively from 4-hydroxy-L-proline. The chiral aminal at C10 was constructed efficiently by means of an Overman-type [3,3] sigmatropic rearrangement of an enamide (see scheme).
Imaoka
Takuya
T
Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo 184-8588, Japan.
Iwamoto
Osamu
O
Noguchi
Kei-ichi
K
Nagasawa
Kazuo
K
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D006576:Heterocyclic Compounds, 4 or More Rings; D010879:Piperazines; C541047:dibromophakellin; C465247:phakellstatin