The Total Synthesis of (±)-Ginkgolide B

The Total Synthesis of (±)-Ginkgolide B

The total synthesis of the potent PAF antagonist ginkgolide B has been accomplished. The complex architecture of ginkgolide B which includes six rings, eleven stereogenic centers, ten oxygenated carbons, and four contiguous fully substituted carbons is a daunting challenge for chemical synthesis. Th...

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Veröffentlicht in:Journal of the American Chemical Society 2000-09, Vol.122 (35), p.8453-8463
Hauptverfasser: Crimmins, Michael T, Pace, Jennifer M, Nantermet, Philippe G, Kim-Meade, Agnes S, Thomas, James B, Watterson, Scott H, Wagman, Allan S
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container_end_page 8463
container_issue 35
container_start_page 8453
container_title Journal of the American Chemical Society
container_volume 122
creator Crimmins, Michael T
Pace, Jennifer M
Nantermet, Philippe G
Kim-Meade, Agnes S
Thomas, James B
Watterson, Scott H
Wagman, Allan S
description The total synthesis of the potent PAF antagonist ginkgolide B has been accomplished. The complex architecture of ginkgolide B which includes six rings, eleven stereogenic centers, ten oxygenated carbons, and four contiguous fully substituted carbons is a daunting challenge for chemical synthesis. The synthesis of ginkgolide B was accomplished through a stereoselective intramolecular photocycloaddition of enone 5 to construct the congested core of the molecule. The photocycloaddition substrate was prepared through technology for the construction of carboalkoxycyclopentenones previously reported from these laboratories. Regioselective cyclobutane fragmentation and further functionalization of the photoadduct 4 provided the key pentacyclic intermediate. Acid-catalyzed rearrangement and epoxide opening were key transformations in the production of ginkgolide B from the pentacyclic intermediate.
doi_str_mv 10.1021/ja001747s
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title The Total Synthesis of (±)-Ginkgolide B
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