A New Stereocontrolled Total Synthesis of the Mast Cell inhibitory Alkaloid, (+)-Monanchorin, via the Wittig Reaction of a Stabilized Ylide with a Cyclic Guanidine Hemiaminal

Karl J. Hale, Liping Wang

Research output: Contribution to journalLetter

10 Citations (Scopus)

Abstract

Abstract Image

An asymmetric total synthesis of the mast cell inhibitor (+)-monanchorin is reported in which a Sharpless AD on 11 and a cyclic sulfate ring opening with an azide feature as key steps. After further manipulation, a novel guanidine-controlled ester reduction provided the guanidine-hemiaminal 25 which underwent Wittig olefination to give 27. Hydrogenation and a second guanidine-controlled reduction of the ester in 28, to obtain aldehyde 29, then set up a trifluoroacetic acid mediated cyclization to give (+)-monanchorin TFA salt.
Original languageEnglish
Pages (from-to)2154-2157
Number of pages4
JournalOrganic Letters
Volume16
Issue number8
Early online date07 Apr 2014
DOIs
Publication statusPublished - 2014

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guanidines
alkaloids
Guanidine
Alkaloids
Mast Cells
esters
Esters
synthesis
Trifluoroacetic Acid
Hydrogenation
Azides
Cyclization
aldehydes
Aldehydes
inhibitors
Sulfates
hydrogenation
manipulators
sulfates
Salts

Cite this

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title = "A New Stereocontrolled Total Synthesis of the Mast Cell inhibitory Alkaloid, (+)-Monanchorin, via the Wittig Reaction of a Stabilized Ylide with a Cyclic Guanidine Hemiaminal",
abstract = "Abstract ImageAn asymmetric total synthesis of the mast cell inhibitor (+)-monanchorin is reported in which a Sharpless AD on 11 and a cyclic sulfate ring opening with an azide feature as key steps. After further manipulation, a novel guanidine-controlled ester reduction provided the guanidine-hemiaminal 25 which underwent Wittig olefination to give 27. Hydrogenation and a second guanidine-controlled reduction of the ester in 28, to obtain aldehyde 29, then set up a trifluoroacetic acid mediated cyclization to give (+)-monanchorin TFA salt.",
author = "Hale, {Karl J.} and Liping Wang",
year = "2014",
doi = "10.1021/ol500616v",
language = "English",
volume = "16",
pages = "2154--2157",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "8",

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TY - JOUR

T1 - A New Stereocontrolled Total Synthesis of the Mast Cell inhibitory Alkaloid, (+)-Monanchorin, via the Wittig Reaction of a Stabilized Ylide with a Cyclic Guanidine Hemiaminal

AU - Hale, Karl J.

AU - Wang, Liping

PY - 2014

Y1 - 2014

N2 - Abstract ImageAn asymmetric total synthesis of the mast cell inhibitor (+)-monanchorin is reported in which a Sharpless AD on 11 and a cyclic sulfate ring opening with an azide feature as key steps. After further manipulation, a novel guanidine-controlled ester reduction provided the guanidine-hemiaminal 25 which underwent Wittig olefination to give 27. Hydrogenation and a second guanidine-controlled reduction of the ester in 28, to obtain aldehyde 29, then set up a trifluoroacetic acid mediated cyclization to give (+)-monanchorin TFA salt.

AB - Abstract ImageAn asymmetric total synthesis of the mast cell inhibitor (+)-monanchorin is reported in which a Sharpless AD on 11 and a cyclic sulfate ring opening with an azide feature as key steps. After further manipulation, a novel guanidine-controlled ester reduction provided the guanidine-hemiaminal 25 which underwent Wittig olefination to give 27. Hydrogenation and a second guanidine-controlled reduction of the ester in 28, to obtain aldehyde 29, then set up a trifluoroacetic acid mediated cyclization to give (+)-monanchorin TFA salt.

U2 - 10.1021/ol500616v

DO - 10.1021/ol500616v

M3 - Letter

VL - 16

SP - 2154

EP - 2157

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 8

ER -