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Dictyostatin   

1 April 2006 4,117 views 4 Comments

dictyostatin.jpg

Phillips and O’Neil. JACS, 2006, ASAP. DOI: 10.1021/ja0609708

Showcasing their (silyloxy)enyne cyclisation (twice) in this neat synthesis, they used a SGHWE to complete the final macrocyclisation in 74%. However, it is their methodology that is most impressive:

dictyostatin_3.jpg

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4 Comments

  • Gaudard says:
    2 April, 2006 at 16:35

    Nice, but they could have used an aldol instead, but i suppose that is what Paterson did.

  • Uncle Bob says:
    2 April, 2006 at 4:07

    It’s pretty cool methodology, coz you could still use it a ‘proper’ protecting group, and do some other stuff before the cyclization. Then you’re only talking about one real step to add in that methyl group

  • anonym says:
    20 April, 2006 at 21:05

    I wonder why those people who synthesize polyol natural products never do alkaloids and vice versa? ;)

  • Tot. Syn. says:
    20 April, 2006 at 22:33

    I think it’s a sort of “when the hat fits” sort of thing… still you get people like Steve Ley and Alois Furstner who do both. However, that’s probably because their methodology fits both product classes.