Generation of the Icetexane Core by Use of a Heck Strategy: Total Synthesis of Taxamairin B
- Authors
- Le, Thuy Quynh; Karmakar, Swastik; Lee, Seonmi; Chai, Uiseong; Le, Minh Hoang; Oh, Chang Ho
- Issue Date
- Oct-2019
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Taxamairin; Icetaxane; Heck reaction; natural product; total synthesis
- Citation
- CHEMISTRYSELECT, v.4, no.40, pp.11926 - 11929
- Indexed
- SCIE
SCOPUS
- Journal Title
- CHEMISTRYSELECT
- Volume
- 4
- Number
- 40
- Start Page
- 11926
- End Page
- 11929
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/147078
- DOI
- 10.1002/slct.201903404
- ISSN
- 2365-6549
- Abstract
- An efficient approach towards the total synthesis of Taxamairin B has been accomplished within 6 steps starting from o-bromobenzylbromide 7 with 45% overall yield. Intramolecular Heck reaction works efficiently to furnish the 6-7-6 fused icetexane scaffold under hydrative condition, which on restructuring affords the key beta,gamma-enedione intermediate. The beta,gamma-double bond has been introduced by the acid catalyzed water assisted elimination of a beta-tertiary alcohol. Later, the beta,gamma-enedione on introduction of requisite unsaturation transforms into Taxamairin B.
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