General Access to Concave-Substituted cis- Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A

被引：4

作者：

Allred, Tyler K. ^{[1
]}

Dieskau, Andre P. ^{[1
]}

Zhao, Peng ^{[1
]}

Lackner, Gregory L. ^{[1
]}

Overman, Larry E. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 23期

基金：

美国国家科学基金会;

关键词：

ALPHA; BETA-UNSATURATED KETONES; ASYMMETRIC-SYNTHESIS; DIVERGENT SYNTHESIS; CARBONYL-COMPOUNDS; CONCISE SYNTHESIS; MOLECULAR-OXYGEN; ALPHA-HYDROXY; ENE REACTIONS; HYDROGENATION; ALCOHOLS;

D O I：

10.1021/acs.joc.0c02273

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The evolution of a strategy to access the family of rearranged spongian diterpenoids harboring a concave-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-one fragment is described. The approach involves late-stage fragment coupling of a tertiary-carbon radical and an electron-deficient double bond to form vicinal quaternary and tertiary stereocenters with high fidelity. A stereoselective Mukaiyama hydration is the key step in the subsequent elaboration of the cis-2,8-dioxabicyclo[3.3.0]octan-3-one moiety. This strategy was utilized in enantioselective total syntheses of (-)-macfarlandin C and (+)-dendrillolide A. An efficient construction of enantiopure tetramethyloctahydronaphthalenes was developed during the construction of (-)-macfarlandin C.

引用

页码：15532 / 15551

页数：20

共 5 条

[1] Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave-Substituted cis-Dioxabicyclo-[3.3.0]octanone Fragment
Allred, Tyler K.
Dieskau, André P.
Zhao, Peng
Lackner, Gregory L.
Overman, Larry E.
[J]. Overman, Larry E. (leoverma@uci.edu), 1600, John Wiley and Sons Inc (59): : 6327 - 6331
[2] Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave-Substituted cis-Dioxabicyclo[3.3.0]octanone Fragment
Allred, Tyler K.
Dieskau, Andre P.
Zhao, Peng
Lackner, Gregory L.
Overman, Larry E.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (15) : 6268 - 6272
[3] Enantioselective syntheses of concave-substituted dioxabicyclo[3.3.0]octanone spongian diterpenoids
Allred, Tyler
Zhao, Peng
Lackner, Greg
Overman, Larry
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[4] Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C
Slutskyy, Yuriy
Jamison, Christopher R.
Zhao, Peng
Lee, Juyeol
Rhee, Young Ho
Overman, Larry E.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (21) : 7192 - 7195
[5] Highly Stereodivergent Construction of a C2-Symmetric cis,cis- and trans,trans-2,6-Dioxabicyclo[3.3.0]octane Framework by Double Intramolecular Amide Enolate Alkylation: Total Synthesis of (+)-Laurenidificin and (+)-Aplysiallene
Shin, Iljin
Jang, Hongjun
Kwak, Soo Yeon
Park, Youngjik
Lee, Dongjoo
Kim, Hyoungsu
Kim, Deukjoon
[J]. ORGANIC LETTERS, 2022, 24 (48) : 8780 - 8785

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