Total synthesis of desoxycyclomarin C and the cyclomarazines A and B

Philipp Barbie; Uli Kazmaier

doi:10.1039/c6ob00801a

Total synthesis of desoxycyclomarin C and the cyclomarazines A and B

Organic & Biomolecular Chemistry ◽

10.1039/c6ob00801a ◽

2016 ◽

Vol 14 (25) ◽

pp. 6055-6064 ◽

Cited By ~ 11

Author(s):

Philipp Barbie ◽

Uli Kazmaier

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Hydroxy Group ◽

Tuberculosis Activity

Removing the β-hydroxy group from the prenylated tryptophan moiety of cyclomarins simplifies the synthesis of these interesting natural products significantly, without having a noteworthy effect on the anti-tuberculosis activity of the cyclomarins.

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α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.17.172 ◽

2021 ◽

Vol 17 ◽

pp. 2570-2584

Author(s):

Scott Benz ◽

Andrew S Murkin

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Asymmetric Synthesis ◽

Hydroxy Group ◽

Tandem Reactions ◽

Aryl Group ◽

The Past

In the presence of a suitable acid or base, α-hydroxyaldehydes, ketones, and imines can undergo isomerization that features the 1,2-shift of an alkyl or aryl group. In the process, the hydroxy group is converted to a carbonyl and the aldehyde/ketone or imine is converted to an alcohol or amine. Such α-ketol/α-iminol rearrangements are used in a wide variety of synthetic applications including asymmetric synthesis, tandem reactions, and the total synthesis and biosynthesis of natural products. This review explores the use of α-ketol rearrangements in these contexts over the past two decades.

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Total synthesis of pyranonaphthoquinone natural products

10.31274/rtd-180813-12358 ◽

1994 ◽

Author(s):

Jun Li

Keyword(s):

Natural Products ◽

Total Synthesis

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Application of Dess-Martin oxidation in total synthesis of natural products

Current Organic Synthesis ◽

10.2174/1570179417666200917102634 ◽

2020 ◽

Vol 17 ◽

Author(s):

Majid M. Heravi ◽

Tayebe Momeni ◽

Vahideh Zadsirjan ◽

Leila Mohammadi

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Selective Oxidation ◽

Secondary Alcohols ◽

Aldehydes And Ketones

: Dess–Martin periodinane (DMP), is a commercially available chemical, frequently being utilized as a mild oxidative agent for the selective oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively. DMP shows several merits over other common oxidative agent such as chromium- and DMSO-based oxidants, thus it is habitually employed in the total synthesis of natural products. In this review, we try to underscore the applications of DMP as an effective oxidant in an appropriate step (steps) in the multistep total synthesis of natural products.

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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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