Total Synthesis of (-)-Lepadiformine A via Radical Translocation-Cyclization Reaction

被引：13

作者：

Shimomura, Masashi ^{[1
]}

Sato, Manabu ^{[1
]}

Azuma, Hiroki ^{[1
]}

Sakata, Juri ^{[1
]}

Tokuyama, Hidetoshi ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 09期

关键词：

TRICYCLIC MARINE ALKALOIDS; CATALYZED CARBONYL ALLYLATION; ALDEHYDE OXIDATION LEVEL; FORMAL TOTAL-SYNTHESIS; NATURAL ENANTIOMER; LEPADIFORMINE; (+/-)-LEPADIFORMINE; (+)-CYLINDRICINE-C; (-)-FASICULARIN; CYLINDRICINES;

D O I：

10.1021/acs.orglett.0c00474

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of (-)-lepadiformine A featuring construction of the 1-azaspiro[4.5]decane skeleton by a highly diastereoselective radical translocation-cyclization reaction of a gamma-lactam derivative bearing a chiral butenolide moiety is described. The enantioselective construction of butenolide is conducted via Krische's catalytic asymmetric allylation protocol. After the radical translocation-cyclization reaction, a hydroxymethyl group at the C-13 position was stereoselectively introduced by a one-pot partial reduction-allylation protocol of the unprotected lactam derivative. Finally, the total synthesis is completed by formation of a C ring.

引用

页码：3313 / 3317

页数：5

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