A Concise Total Synthesis of (±)-Mesembrine

A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson–Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.

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Total synthesis of clavosolide A via tandem allylic oxidation/oxa-conjugate addition reaction

Tetrahedron Letters ◽

10.1016/j.tetlet.2014.11.135 ◽

2015 ◽

Vol 56 (23) ◽

pp. 3120-3122 ◽

Cited By ~ 10

Author(s):

Joseph B. Baker ◽

Hyoungsu Kim ◽

Jiyong Hong

Keyword(s):

Total Synthesis ◽

Addition Reaction ◽

Conjugate Addition ◽

Allylic Oxidation

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Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction

Natural Products and Bioprospecting ◽

10.1007/s13659-020-00276-8 ◽

2020 ◽

Author(s):

Yuan Huang ◽

Fanglin Xue ◽

Hengmao Liu ◽

Fei Xue ◽

Xiao-Yu Liu ◽

...

Keyword(s):

Total Synthesis ◽

Visible Light ◽

Claisen Rearrangement ◽

Cascade Reaction ◽

Ring System ◽

Asymmetric Total Synthesis ◽

Radical Cascade ◽

Key Features ◽

Quaternary Stereocenter ◽

Visible Light Photocatalytic

Abstract An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter. Graphic Abstract

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Stereoselective Synthesis of 2,6-trans-Tetrahydropyran via Primary Diamine-Catalyzed Oxa-Conjugate Addition Reaction of α,β-Unsaturated Ketone: Total Synthesis of Psymberin

Organic Letters ◽

10.1021/ol2024289 ◽

2011 ◽

Vol 13 (21) ◽

pp. 5816-5819 ◽

Cited By ~ 44

Author(s):

Seong Rim Byeon ◽

Heekwang Park ◽

Hyoungsu Kim ◽

Jiyong Hong

Keyword(s):

Total Synthesis ◽

Stereoselective Synthesis ◽

Addition Reaction ◽

Conjugate Addition ◽

Unsaturated Ketone

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Enantioselective Total Synthesis of atrans-Hydrindane Rings/Side-Chain Building-Block of Vitamin D− Asymmetric Induction in an Acid-Catalyzed Conjugate-Addition Reaction

European Journal of Organic Chemistry ◽

10.1002/ejoc.200300611 ◽

2004 ◽

Vol 2004 (4) ◽

pp. 783-799 ◽

Cited By ~ 11

Author(s):

Evgueni Gorobets ◽

Viatcheslav Stepanenko ◽

Jerzy Wicha

Keyword(s):

Vitamin D ◽

Total Synthesis ◽

Building Block ◽

Addition Reaction ◽

Conjugate Addition ◽

Asymmetric Induction ◽

Side Chain ◽

Enantioselective Total Synthesis ◽

Acid Catalyzed

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Concise total synthesis of (±)-aspidospermidine

Organic & Biomolecular Chemistry ◽

10.1039/c5ob00228a ◽

2015 ◽

Vol 13 (18) ◽

pp. 5255-5259 ◽

Cited By ~ 19

Author(s):

Haichen Ma ◽

Xingang Xie ◽

Peng Jing ◽

Weiwei Zhang ◽

Xuegong She

Keyword(s):

Total Synthesis ◽

Addition Reaction ◽

Conjugate Addition ◽

One Pot ◽

Carbonyl Reduction

(±)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. The key step of the strategy is a one-pot carbonyl reduction/iminium formation/intramolecular conjugate addition reaction that may be applied for the synthesis of other kinds of Aspidosperma alkaloids.

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