TOTAL SYNTHESES OF THE MARINE SPONGE PIGMENTS FASCAPLYSIN AND HOMOFASCAPLYSIN-B AND HOMOFASCAPLYSIN-C | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

1205532

Reference Type

Journal Article

Title

TOTAL SYNTHESES OF THE MARINE SPONGE PIGMENTS FASCAPLYSIN AND HOMOFASCAPLYSIN-B AND HOMOFASCAPLYSIN-C

Author(s)

Gribble, GW; Pelcman, B

Year

1992

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Volume

Issue

Page Numbers

3636-3642

DOI

10.1021/jo00039a024

URL

https://pubs.acs.org/doi/abs/10.1021/jo00039a024
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Abstract

The Fascaplysinopsis spp. marine sponge pigments fascaplysin (1), homofascaplysin B (4), and homofascaplysin C (5) have been synthesized by peracid oxidation, reaction with oxalyl chloride/methanol, or Vilsmeier formylation, respectively, of the keystone intermediate 12H-pyrido[1,2-a:3,4-b]diindole (7). The versatile 7 was prepared from indole (17) in six steps (78% yield), a sequence in which the key reaction is the trifluoroacetic acid-induced ring closure of diindole 15, followed by Pd/C-catalyzed dehydrogenation of the crude mixture of cyclized products 25, 26, to give 7 in 93% yield from 15. © 1992, American Chemical Society. All rights reserved.