A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B

被引：7

作者：

Natho, Philipp ^{[1
]}

Allen, Lewis A. T. ^{[1
]}

Parsons, Philip J. ^{[1
]}

机构：

[1] Imperial Coll London, Dept Chem, London W12 0BZ, England

来源：

SYNLETT | 2023年 / 34卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

total synthesis; ring expansion; cyclization; antifungal agents; rearrangement; ALKALOIDS CARBAZOMYCIN; ORGANIC-SYNTHESIS; AMINATION; IDENTIFICATION; ANTIBIOTICS; COMPLEXES; ROOTS; ROUTE;

D O I：

10.1055/s-0042-1751411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transition-metal-free total syntheses of the oxygenated carbazole natural products glycoborine, carbazomycin A and carbazomycin B are reported. The key step involves an NBS-mediated cyclobutanol ring expansion to 4-tetralones for the preparation of the tricyclic carbazole core.

引用

页码：937 / 942

页数：6

共 38 条

[21] Synthesis of tetrahydrofuro[2,3-b][1]benzopyranones by the ring-expansion reaction of methanochromanone with symmetric ketones
Sugita, Y
Kawai, K
Yokoe, I
HETEROCYCLES, 2000, 53 (03) : 657 - +
[22] Asymmetric Synthesis of Dihydronaphthoquinones Containing Adjacent Stereocenters via a Sulfa-Michael Addition Triggered Ring-Expansion Approach
Hu, Zhi-Peng
Zhuang, Zhe
Liao, Wei-Wei
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4627 - 4637
[23] Total synthesis of aspinolide B: a ring-closing metathesis approach
Ghosh, Subhash
Rao, R. Vengal
TETRAHEDRON LETTERS, 2007, 48 (39) : 6937 - 6940
[24] Ring-expansion of 2-methylbenzo[b]furan to 3-hydroxychromen-4-one: A potential approach to a flavonol skeleton
Ishikawa, T
Miwa, C
HETEROCYCLES, 1997, 45 (11) : 2273 - 2276
[25] Synthesis of fused B,N-heterocycles by alkyne cleavage, NHC ring-expansion and C-H activation at a diboryne
Brueckner, Tobias
Arrowsmith, Merle
Hess, Merlin
Hammond, Kai
Mueller, Marcel
Braunschweig, Holger
CHEMICAL COMMUNICATIONS, 2019, 55 (47) : 6700 - 6703
[26] Total Synthesis of Marine Alkaloids Motuporamines A and B via Ring Expansion of Cyclic β-Keto Esters
Song, Zi-Jie
Meng, Shu-Yu
Wang, Quan-Rui
ACS OMEGA, 2021, 6 (01): : 881 - 888
[27] N-Bromosuccinimide-Induced Aminocyclization-Aziridine Ring-Expansion Cascade: An Asymmetric and Highly Stereoselective Approach toward the Synthesis of Azepane
Zhou, Jing
Yeung, Ying-Yeung
ORGANIC LETTERS, 2014, 16 (08) : 2134 - 2137
[28] DITERPENOID TOTAL SYNTHESIS, AN A-]B-]C APPROACH .11. C-RING DEOXY AROMATIC SYSTEMS - TOTAL SYNTHESIS OF METHYL (+/-)-DEHYDROABIETATE
MEYER, WL
SIGEL, CW
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (16): : 2769 - 2771
[29] Stereospecific Approach to the Synthesis of Ring-A Oxygenated Sarpagine Indole Alkaloids. Total Synthesis of the Dimeric Indole Alkaloid P-(+)-Dispegatrine and Six Other Monomeric Indole Alkaloids
Edwankar, Chitra R.
Edwankar, Rahul V.
Namjoshi, Ojas A.
Liao, Xuebin
Cook, James M.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13): : 6471 - 6487
[30] Organoboron-Based Allylation Approach to the Total Synthesis of the Medium-Ring Dilactone (+)-Antimycin A1b
Janetzko, John
Batey, Robert A.
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16): : 7415 - 7424

← 1 2 3 4 →