An approach toward the synthesis of PPAP natural product garsubellin A: construction of the tricyclic core

被引：12
作者：
Mehta, Goverdhan [1 ,2 ]
Bera, Mrinal K. [1 ,2 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
[2] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
来源：
TETRAHEDRON | 2013年 / 69卷 / 07期
关键词：
Dimedone; PPAP natural product; Neurodegenerative disorder; Alzheimers' disease; Aldol reaction; PCC oxidation; POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; ALKYLATIVE DEAROMATIZATION-ANNULATION; ASYMMETRIC TOTAL-SYNTHESIS; FLORAL RESINS; REGIOSELECTIVE LITHIATION; ABSOLUTE-CONFIGURATION; BRIDGEHEAD LITHIATION; BICYCLIC SYSTEM; A SYNTHESIS; HYPERFORIN;
D O I：
10.1016/j.tet.2012.12.066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In a study directed toward the bioactive natural product garsubellin A, an expedient route to the bicyclo [3.3.1]nonan-9-one bearing tricyclic core, with a bridgehead anchored tetrahydrofuran ring, is delineated. The approach emanating from commercially available dimedone involved a DIBAL-H mediated retro aldol/re-aldol cyclization cascade and a PCC mediated oxidative cyclization as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.
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收藏
页码：1815 / 1821
页数：7
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