2011
DOI: 10.1002/chem.201101082
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Synthesis of the Anti‐HIV Agent (−)‐Hyperolactone C by Using Oxonium Ylide Formation–Rearrangement

Abstract: Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product.

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Cited by 35 publications
(18 citation statements)
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“…1,2 Besides, it is also used to synthesize antidepressants and anti-HIV agents. 3,4 Conventionally, styrene oxide is synthesized via a chlorohydrin epoxidation route. 5,6 However, the use of hazardous precursors and undesired waste products have urged the need for a greener alternative synthesis route.…”
Section: Introductionmentioning
confidence: 99%
“…1,2 Besides, it is also used to synthesize antidepressants and anti-HIV agents. 3,4 Conventionally, styrene oxide is synthesized via a chlorohydrin epoxidation route. 5,6 However, the use of hazardous precursors and undesired waste products have urged the need for a greener alternative synthesis route.…”
Section: Introductionmentioning
confidence: 99%
“…Subsequently, the field of oxonium ylide rearrangements gradually came into focus in modern organic chemistry, and not surprisingly, thanks to the ability to quickly generate molecular complexity from well accessible carboxylic acid derivatives, these rearrangement reactions have in recent years also made their way into strategies for the total synthesis of structurally sophisticated natural products …”
mentioning
confidence: 99%
“…Dihydrofurans and their derivatives are important structural units frequently found in many natural products, agrochemicals, and pharmaceuticals . Renowned examples include amiodarone (for the treatment of cardiopathy and breast cancer), flurtamone (selective herbicide), rofecoxib (anti-inflammatory drug), and hyperlactone C (anti-HIV agent) . Therefore, the direct conversion of nitro compounds into dihydrofuran derivatives has attracted the interest of many chemists.…”
Section: Introductionmentioning
confidence: 99%