Synthesis of the Spiroacetal‐Containing anti‐Helicobacter pylori Agents CJ‐12,954 and CJ‐13,014.

Brimble, Margaret A.; Bryant, Christina J.

doi:10.1002/chin.200711219

Cited by 2 publications

(2 citation statements)

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“…In particular, spiroketals represent a structural feature of many biomedically relevant natural and non-natural systems [ 99 , 100 , 101 , 102 ]. Several methods have been developed for the synthesis of spiroketals, the most common being perhaps the cyclocondensation of ketone diols [ 103 , 104 ]. Nevertheless, gold catalyzed cycloisomerization on alkynediols has emerged as an efficient strategy to build complex ketal systems in just one step, offering specific advantages.…”

Section: Cycloisomerization Processes Involving Carbon-heteroatom mentioning

confidence: 99%

Gold-Catalyzed Cyclizations of Alkynol-Based Compounds: Synthesis of Natural Products and Derivatives

2011

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The last decade has witnessed dramatic growth in the number of reactions catalyzed by gold complexes because of their powerful soft Lewis acid nature. In particular, the gold-catalyzed activation of propargylic compounds has progressively emerged in recent years. Some of these gold-catalyzed reactions in alkynes have been optimized and show significant utility in organic synthesis. Thus, apart from significant methodology work, in the meantime gold-catalyzed cyclizations in alkynol derivatives have become an efficient tool in total synthesis. However, there is a lack of specific review articles covering the joined importance of both gold salts and alkynol-based compounds for the synthesis of natural products and derivatives. The aim of this Review is to survey the chemistry of alkynol derivatives under gold-catalyzed cyclization conditions and its utility in total synthesis, concentrating on the advances that have been made in the last decade, and in particular in the last quinquennium.

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Section: Cycloisomerization Processes Involving Carbon-heteroatom mentioning

confidence: 99%

Gold-Catalyzed Cyclizations of Alkynol-Based Compounds: Synthesis of Natural Products and Derivatives

2011

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“…Brimble et al . first synthesized the anti- helicobacter pylori agents CJ-12,954 and CJ-13,014 based on the union of hetercycle-activated spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragment [ 47 ]. The key step in this synthesis is a modified Julia olefination of phthalide aldehyde and heterocycle-activated sulfones.…”

Section: Asymmetric Total Synthesis Of Natural Spiroketalsmentioning

confidence: 99%