Total syntheses of (±)-penicibilaenes A and B via intramolecular aldol condensation

被引：6

作者：

Matsuo, Rintaro ^{[1
]}

Watanabe, Ayumu ^{[1
]}

Kamo, Shogo ^{[1
]}

Matsuzawa, Akinobu ^{[1
]}

Sugita, Kazuyuki ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Dept Synthet Med Chem, Shinagawa Ku, 2-4-41 Ebara, Tokyo 1428501, Japan

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 21期

关键词：

CONJUGATE ADDITION; ALCOHOLS;

D O I：

10.1039/d1qo01251g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, concise total syntheses of Peniclillium sesquiterpenes (+/-)-Penicibilaenes A and B are described. This approach involves an effective intramolecular aldol condensation to construct a bicyclic skeleton, a stereoselective rhodium-catalyzed 1,4-addition, a ring-closing metathesis, and several effective transformations that lead to (+/-)-penicibilaenes A and B with longest linear sequences of 12 and 13 steps, respectively. These transformations utilize commercial materials and are achieved in 4.0% overall yields for both compounds.

引用

页码：6063 / 6066

页数：4

共 50 条

[21] Enantioselective total synthesis of (+)-galbulin via organocatalytic domino Michael-Michael-aldol condensation
Hong, Bor-Cherng
Hsu, Che-Sheng
Lee, Gene-Hsiang
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (18) : 2385 - 2387
[22] Total syntheses of carbohydrates: Organocatalyzed aldol additions of dihydroxyacetone
Markert, Morris
Mahrwald, Rainer
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) : 40 - 48
[23] PREPARATION OF HETEROCYCLIC AMINO-ACIDS VIA INTRAMOLECULAR MUKAIYAMA ALDOL CONDENSATION - SYNTHESIS OF A NOVEL CYCLOLEUCINE ANALOG
WALKER, DM
LOGUSCH, EW
[J]. TETRAHEDRON LETTERS, 1989, 30 (10) : 1181 - 1184
[24] Convenient synthetic route to a dehydrorotenoid via selective intramolecular aldol condensation of 1,2-diaryl diketone
Tummatorn, Jumreang
Khorphueng, Prapas
Petsom, Amorn
Muangsin, Nongnuch
Chaichit, Narongsak
Roengsumran, Sophon
[J]. TETRAHEDRON, 2007, 63 (48) : 11878 - 11885
[25] Synthesis of β-Naphthols and Naphthofuranones from ortho-Alkynylarylketones via Sequential AgTFA-Catalyzed Ketonization-Intramolecular Aldol Condensation: A Total Synthesis of Negundin A
Nimnual, Phongprapan
Norseeda, Krissada
Akkachairin, Bhornrawin
Tummatorn, Jumreang
Laohapaisan, Pavitra
Supantanapong, Nantamon
Chuangsoongnern, Pennapa
Thongsornkleeb, Charnsak
Sittihan, Satapanawat
Ruchirawat, Somsak
Rodphon, Warabhorn
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (05) : 932 - 945
[26] Asymmetric Divergent Total Syntheses of (+)-Decursivine and (+)-Serotobenine via Intramolecular Fischer Indole Synthesis
Kim, Dong-Hyun
Kim, Hyo-Mi
Lim, Ji-Su
Lee, Hyun-Woo
Cho, Cheon-Gyu
[J]. ORGANIC LETTERS, 2022, 24 (15) : 2873 - 2877
[27] Asymmetric total syntheses of hydroxylated piperidine alkaloids via the intramolecular reaction of γ-aminoallylstannane with aldehyde
Kadota, I
Kawada, M
Muramatsu, Y
Yamamoto, Y
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (23) : 3887 - 3893
[28] ASYMMETRIC TOTAL SYNTHESES OF (-)-TYLOPHORINE VIA THE HIGHLY ENANTIOSELECTIVE INTRAMOLECULAR DOUBLE MICHAEL REACTION
IHARA, M
TAKINO, Y
FUKUMOTO, K
KAMETANI, T
[J]. TETRAHEDRON LETTERS, 1988, 29 (33) : 4135 - 4138
[29] Total synthesis of 3-epi-(+)-lycoricidine from Gamer aldehyde via intramolecular aldol cyclization
Bera, Saurav
Das, Sanjit Kumar
Saha, Hash
Panda, Gautam
[J]. TETRAHEDRON LETTERS, 2015, 56 (01) : 146 - 149
[30] ERYTHRO-SELECTIVE ALDOL CONDENSATION VIA ENAMINOSILANES
ANDO, W
TSUMAKI, H
[J]. CHEMISTRY LETTERS, 1983, (09) : 1409 - 1412

← 1 2 3 4 5 →