Recent Progress in the Total Synthesis of Dolabellane and Dolastane Diterpenes

Non-Enzymatic Desymmetrization Reactions in Aqueous Media

Symmetry ◽

10.3390/sym13040720 ◽

2021 ◽

Vol 13 (4) ◽

pp. 720

Author(s):

Satomi Niwayama

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Functional Groups ◽

Organic Compounds ◽

Recent Progress ◽

Aqueous Media ◽

Building Blocks ◽

Organic Reactions ◽

Environmentally Benign ◽

Enzymatic Desymmetrization

Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes.

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Recent progress toward synthesis of chlorosulfolipids: total synthesis and methodology

Tetrahedron Letters ◽

10.1016/j.tetlet.2014.03.082 ◽

2014 ◽

Vol 55 (19) ◽

pp. 3003-3012 ◽

Cited By ~ 27

Author(s):

Taiki Umezawa ◽

Fuyuhiko Matsuda

Keyword(s):

Total Synthesis ◽

Recent Progress

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Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies

Canadian Journal of Chemistry ◽

10.1139/v06-073 ◽

2006 ◽

Vol 84 (10) ◽

pp. 1226-1241 ◽

Cited By ~ 14

Author(s):

Peter Wipf ◽

Michel Grenon

Keyword(s):

Transition Metal ◽

Total Synthesis ◽

Recent Progress ◽

Furan Ring ◽

Addition Reaction ◽

Thermal Conditions ◽

Preliminary Results ◽

Keto Esters ◽

New Methodologies ◽

Metal Catalyzed

Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal-catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation.Key words: 1,6-addition, organocuprates, catalytic desymmetrization, furan cyclization, microwave.

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ChemInform Abstract: Recent Progress in Isolation, Bioactivity Evaluation and Total Synthesis of Diarylheptanoids.

ChemInform ◽

10.1002/chin.200109261 ◽

2001 ◽

Vol 32 (9) ◽

pp. no-no

Author(s):

Jieping Zhu ◽

G. Islas-Gonzalez ◽

M. Bois-Choussy

Keyword(s):

Total Synthesis ◽

Recent Progress

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Bioinspired Total Synthesis of Marine Anti-Cancer Meroterpenoids Dysideanone B and Dysiherbol A and Structure Revision of Dysiherbol A

Synlett ◽

10.1055/a-1546-2572 ◽

2021 ◽

Author(s):

Zhaoyong Lu ◽

Chuanke Chong

Keyword(s):

Total Synthesis ◽

Heck Reaction ◽

Recent Progress ◽

Benzyl Bromide ◽

Radical Cyclization ◽

Ethoxy Group ◽

Anti Cancer ◽

Structure Revision ◽

A Site ◽

Intramolecular Heck Reaction

Our recent progress on the total synthesis of marine anti-cancer sesquiterpene quinone/hydroquinone dysideanone B and dysiherbol A was briefly highlighted. This success relied on some key transformations. The union of the terpene and quinone/hydroquinone moieties was realized through a site and stereoselective α-position alkylation of Wieland–Miescher ketone derivative with a bulky benzyl bromide. The 6/6/6/6-tetracycle of dysideanone B was constructed using an intramolecular radical cyclization and the 6/6/5/6-fused core structure of dysiherbol A was forged by an intramolecular Heck reaction, respectively. The possible origin of ethoxy group in dysideanone B was revealed by mimicking the isolation conditions at a late-stage. The structure of dysiherbol A was revised through the total synthesis of this natural product. Schmalz’s synthesis of dysiherbol A was also included.

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