Asymmetric Total Synthesis of (-)-(3R)-Inthomycin C

被引：17

作者：

Balcells, Sandra ^{[1
]}

Haughey, Maxwell B. ^{[1
]}

Walker, Johannes C. L. ^{[1
]}

Josa-Cullere, Laia ^{[1
]}

Towers, Christopher ^{[2
]}

Donohoe, Timothy J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

[2] Univ Oxford, Dept Oncol, Old Rd Campus Res Bldg,Roosevelt Dr, Oxford OX3 7DQ, England

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 12期

关键词：

CELLULOSE BIOSYNTHESIS; PYRROLIDINONE CORE; FORMAL SYNTHESIS; PHTHOXAZOLIN; INHIBITOR; OXAZOLES;

D O I：

10.1021/acs.orglett.8b01370

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short (10 step) and efficient (15% overall yield) synthesis of the natural product (-)-(3R)-inthomycin C is reported. The key steps comprise three C-C bond-forming reactions: (i) a vinylogous Mukaiyama aldol, (ii) an olefin cross-metathesis reaction, and (iii) an asymmetric Mukaiyama-Kiyooka aldol. This route is notable for its brevity and has the advantage of lacking stoichiometric tin promoted cross-coupling reactions present in previous approaches. Initial investigations on the biological activity of (-)-(3R)-inthomycin C and structural analogues on human cancer cell lines are also described for the first time.

引用

页码：3583 / 3586

页数：4

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