Studies toward the Synthesis of Iriomoteolide-2a: Construction of the C(6)–C(28) Fragment

Studies toward the Synthesis of Iriomoteolide-2a: Construction of the C(6)–C(28) Fragment

The synthesis of an appropriately functionalized advanced C(6–28) fragment (3) of the marine macrolide iriomoteolide-2a (1) has been achieved in a highly efficient manner. The C(6)–C(18) fragment of 1 is prepared via a radical cyclization of a vinyl ether intermediate and palladium-promoted hydrosta...

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Veröffentlicht in:Organic letters 2018-04, Vol.20 (8), p.2213-2215
Hauptverfasser: Wang, Lushun, Wu, Fusong, Jia, Xuelei, Xu, Zhengshuang, Guo, Yian, Ye, Tao
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container_end_page 2215
container_issue 8
container_start_page 2213
container_title Organic letters
container_volume 20
creator Wang, Lushun
Wu, Fusong
Jia, Xuelei
Xu, Zhengshuang
Guo, Yian
Ye, Tao
description The synthesis of an appropriately functionalized advanced C(6–28) fragment (3) of the marine macrolide iriomoteolide-2a (1) has been achieved in a highly efficient manner. The C(6)–C(18) fragment of 1 is prepared via a radical cyclization of a vinyl ether intermediate and palladium-promoted hydrostannylation/iodination. Paterson aldol reaction and Peterson olefination are used to construct the C(19)–C(28) fragment. The union of the C(6)–C(18) and C(19)–C(28) fragments is accomplished via a Suzuki–Miyaura coupling reaction.
doi_str_mv 10.1021/acs.orglett.8b00542
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title Studies toward the Synthesis of Iriomoteolide-2a: Construction of the C(6)–C(28) Fragment
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