Structural verification of petromyzestrosterol by total syntheses of both C14-epimers of its 3-<i>O</i>-methyl derivative

Nakazaki, Atsuo; Kawai, Maho; Nishikawa, Toshio

doi:10.1039/d2ob01047j

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob01047j

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Structural verification of petromyzestrosterol by total syntheses of both C14-epimers of its 3-O-methyl derivative

Atsuo Nakazaki

Maho Kawai

Toshio Nishikawa

Abstract: The structure of petromyzestrosterol, a pheromonal steroid of the sea lamprey, was verified by total syntheses of both C14-epimers of its 3-O-methyl derivative.

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Cited by 2 publications

References 15 publications

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Total Synthesis of 19-Nordigitoxigenin, An Antiaroside Y Aglycon

Matsumura,

Nishikawa,

Nakazaki

2023

J. Org. Chem.

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The first total synthesis of 19-nordigitoxigenin, an aglycon of antiroside Y, has been achieved. The key steps of our synthesis are (i) construction of the 19-norsteroid ring system via a Mizoroki–Heck reaction between a bromoanisole corresponding to the A-ring and cyclic alkene incorporating the CD-rings, followed by a Friedel–Crafts-type cyclodehydration, and (ii) incorporation of the butenolide moiety at C17 via a silyl-tethered radical cyclization and subsequent ozone oxidation.

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Total Synthesis of 19-Nordigitoxigenin, An Antiaroside Y Aglycon

Matsumura,

Nishikawa,

Nakazaki

2023

J. Org. Chem.

Self Cite

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An Asymmetric Total Synthesis of Picrotoxinin through a Mizoroki–Heck Reaction

Matsumura

Nishikawa

Nakazaki

2022

Synlett

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An asymmetric total synthesis of picrotoxinin was achieved, with a Mizoroki-Heck reaction of an enantioenriched tricyclic lactone with isopropenyl bromide as the key transformation, enabling the highly diastereoselective introduction of the requisite C4-isopropenyl group. After functional group manipulations including carbonylation, bromoetherification, epoxidation and dihydroxylation, picrotoxinin was obtained in moderate to good yield.

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Structural verification of petromyzestrosterol by total syntheses of both C14-epimers of its 3-O-methyl derivative

Abstract: The structure of petromyzestrosterol, a pheromonal steroid of the sea lamprey, was verified by total syntheses of both C14-epimers of its 3-O-methyl derivative.

Cited by 2 publications

References 15 publications

Total Synthesis of 19-Nordigitoxigenin, An Antiaroside Y Aglycon

Total Synthesis of 19-Nordigitoxigenin, An Antiaroside Y Aglycon

An Asymmetric Total Synthesis of Picrotoxinin through a Mizoroki–Heck Reaction

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