scispace - formally typeset
Search or ask a question
Topic

Total synthesis

About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.


Papers
More filters
Journal ArticleDOI
TL;DR: This report describes a rapid asymmetric total synthesis of the tetrahydroisoquinoline antitumor antibiotic (-)-quinocarcin using a mild fluoride-induced aryne annulation developed in the laboratories to build a key isoquinoline-containing intermediate comprising the entire carbon scaffold of the natural product.
Abstract: Described in this report is a rapid asymmetric total synthesis of the tetrahydroisoquinoline antitumor antibiotic (−)-quinocarcin. The sequence employs a mild fluoride-induced aryne annulation developed in our laboratories to build a key isoquinoline-containing intermediate comprising the entire carbon scaffold of the natural product. This intermediate is advanced through six additional steps to the target alkaloid, providing the shortest synthetic route to (−)-quinocarcin reported to date.

89 citations

Journal ArticleDOI
TL;DR: A biosynthetically inspired synthesis of (+)-liphagal has been achieved from (+)-sclareolide in 13 steps (9% overall yield) using a biomimetic ring expansion of a highly stabilized benzylic carbocation.

89 citations

Journal ArticleDOI
TL;DR: The first synthesis of (−)-FR901483 (1) has been accomplished in 2% overall yield from O-methyltyrosine methyl ester (31) in 22 steps establishing the absolute stereochemistry of the natural product as discussed by the authors.
Abstract: The first synthesis of the immunosuppressant (−)-FR901483 (1) has been accomplished in 2% overall yield from O-methyltyrosine methyl ester (31) in 22 steps establishing the absolute stereochemistry of the natural product. A 1,3-dipolar cycloaddition of nitrone 5b with ethyl acrylate gave predominantly isoxazolidine 4b that was hydrogenated to give azaspirolactam 3b with the correct absolute and relative stereochemistry for the synthesis of 1. Elaboration of 3b to keto aldehyde 38 and an intramolecular aldol reaction gave tricyclic keto alcohol 40 with reasonable selectivity using KO-t-Bu in t-BuOH. Further elaboration afforded (−)-1 in 9 steps with spectral data identical to that of the natural product.

89 citations

Journal ArticleDOI
TL;DR: The first biomimetic enanti-lective total synthesis of (-)-communesin F based on a late-stage heterodimerization and aminal exchange is described in this paper.
Abstract: The first biomimetic enantioselective total synthesis of (-)-communesin F based on a late-stage heterodimerization and aminal exchange is described. Our synthesis features the expedient diazene-directed assembly of two advanced fragments to secure the congested C3a-C3a' linkage in three steps, followed by a highly efficient biogenetically inspired aminal reorganization to access the heptacyclic communesin core in only two additional steps. Enantioselective syntheses of the two fragments were developed, with highlights including the catalytic asymmetric halocyclization and diastereoselective oxyamination reactions of tryptamine derivatives, a stereoselective sulfinimine allylation, and an efficient cyclotryptamine-C3a-sulfamate synthesis by either a new silver-promoted nucleophilic amination or a rhodium-catalyzed C-H amination protocol. The versatile syntheses of the fragments, their stereocontrolled assembly, and the efficient aminal exchange as supported by in situ monitoring experiments, in addition to the final stage N1'-acylation of the communesin core, provide a highly convergent synthesis of (-)-communesin F.

89 citations


Network Information
Related Topics (5)
Cycloaddition
39.9K papers, 728.7K citations
98% related
Enantioselective synthesis
58.1K papers, 1.6M citations
98% related
Aryl
95.6K papers, 1.3M citations
97% related
Intramolecular force
41.6K papers, 772.2K citations
93% related
Lewis acids and bases
29.5K papers, 631.7K citations
93% related
Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023245
2022592
2021479
2020451
2019497
2018551