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

[41] Total synthesis of penmacric acids via an intermolecular radical addition reaction
Ueda, Masafumi
Ono, Ayako
Nakao, Dai
Matsuno, Kenji
Naito, Takeaki
Miyata, Okiko
TETRAHEDRON, 2013, 69 (33) : 6866 - 6874
[42] A formal synthesis of (+)-α-allokainic acid via sulfanyl radical addition-cyclization reaction
Miyata, O
Ozawa, Y
Ninomiya, T
Aoe, K
Hiramatsu, H
Naito, T
HETEROCYCLES, 1997, 46 : 321 - 333
[43] Sulfone-mediated total synthesis of (±)-lepadiformine
Caldwell, John J.
Craig, Donald
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) : 2631 - 2634
[44] Formal total synthesis of (±)-bisabolangelone by using a radical cyclization
Cossy, J
Bellosta, V
Gille, B
COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE, 2001, 4 (06): : 427 - 429
[45] Formal total synthesis of (±)-vindoline by tandem radical cyclization
Zhou, SZ
Bommezijn, S
Murphy, JA
ORGANIC LETTERS, 2002, 4 (03) : 443 - 445
[46] A radical cyclization strategy for the concise total synthesis of (+/-)-geissoschizine
Takayama, H
Watanabe, F
Kitajima, M
Aimi, N
TETRAHEDRON LETTERS, 1997, 38 (30) : 5307 - 5310
[47] Total synthesis of (+/-)-epilupinine via an organoyttrium-catalyzed sequential cyclization/silylation reaction
Molander, GA
Nichols, PJ
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17): : 6040 - 6043
[48] Total Synthesis of (+)-seco-C-Oleanane via Stepwise Controlled Radical Cascade Cyclization
Domingo, Victoriano
Arteaga, Jesus F.
Lopez Perez, Jose Luis
Pelaez, Rafael
Quilez del Moral, Jose F.
Barrero, Alejandro F.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 341 - 350
[49] A new total synthesis of the marine tunicate alkaloid lepadiformine
Sun, P
Sun, CX
Weinreb, SM
ORGANIC LETTERS, 2001, 3 (22) : 3507 - 3510
[50] Total synthesis of ent-lycoricidine via a thiyl radical addition-cyclization sequence
Keck, GE
Wager, TT
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24): : 8366 - 8367

← 1 2 3 4 5 →