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

共 50 条

[1] Total Synthesis of (±)-Lepadiformine A via Radical Translocation-Cyclization Reaction
Fujitani, Manabu
Tsuchiya, Masami
Okano, Kentaro
Takasu, Kiyosei
Ihara, Masataka
Tokuyama, Hidetoshi
SYNLETT, 2010, (05) : 822 - 826
[2] Total Synthesis of (-)-Histrionicotoxin through a Stereoselective Radical Translocation-Cyclization Reaction
Sato, Manabu
Azuma, Hiroki
Daigaku, Akihiro
Sato, Sota
Takasu, Kiyosei
Okano, Kentaro
Tokuyama, Hidetoshi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (04) : 1087 - 1091
[3] Total Synthesis of Leuconoxine, Melodinine E, and Mersicarpine through Radical Translocation-Cyclization Cascade
Kim, Ryan
Ferreira, Andrew J.
Beaudry, Christopher M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (36) : 12595 - 12598
[4] Synthesis of 4′-Spironucleoside via Radical Translocation Cyclization Reaction
DANG Shao-feng
ChemicalResearchinChineseUniversities, 2008, (04) : 473 - 476
[5] Total synthesis of the marine alkaloid (±)-lepadiformine via a radical carboazidation
Schar, P
Renaud, P
ORGANIC LETTERS, 2006, 8 (08) : 1569 - 1571
[6] TOTAL SYNTHESIS OF (+/-)-ACORADIENE VIA RADICAL CYCLIZATION
CHEN, YJ
LIN, WY
TETRAHEDRON, 1993, 49 (45) : 10263 - 10270
[7] Total Synthesis of (±)-Goniomitine via Radical Translocation
Vellucci, Jessica K.
Beaudry, Christopher M.
ORGANIC LETTERS, 2015, 17 (18) : 4558 - 4560
[8] Preparation of Five-Membered Rings via the Translocation-Cyclization of Vinyl Radicals
Denes, Fabrice
Beaufils, Florent
Renaud, Philippe
SYNLETT, 2008, (16) : 2389 - 2399
[9] TOTAL SYNTHESIS OF (+/-)-LAURENE AND EPILAURENE BY RADICAL CYCLIZATION REACTION
SRIKRISHNA, A
SUNDERBABU, G
TETRAHEDRON LETTERS, 1989, 30 (27) : 3561 - 3562
[10] Total synthesis of (±)-lepadiformine via an amidoacrolein cycloaddition
Greshock, TJ
Funk, RL
ORGANIC LETTERS, 2001, 3 (22) : 3511 - 3514

← 1 2 3 4 5 →