Stereoselective Synthesis of (4S,6S)-6-Hydroxy-4-undecanolide: A Pheromone of the Giant White Butterfly Idea leuconoe

Yadav, J. S.; Reddy, Poli Adi Narayana; Ather, Hissana; Kumar, Alleni Suman; Prasad, A. R.; Reddy, B. V. Subba; Khazim, Ahmad Al

doi:10.1055/s-0031-1289671

Cited by 9 publications

(2 citation statements)

References 6 publications

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“…The stereoselective synthesis of (4S,6S)-6-hydroxy-4-undecanolide, a major pheromone component in the secretion of Idea leuconoe has been accomplished by employing Prins cyclization, hydroboration/oxidation as the key steps. [32] The synthetic approach commenced from a chiral homoallylic Scheme 27. Synthesis of (+)-Neopeltolide.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

“…The stereoselective synthesis of (4 S ,6 S )‐6‐hydroxy‐4‐undecanolide, a major pheromone component in the secretion of Idea leuconoe has been accomplished by employing Prins cyclization, hydroboration/oxidation as the key steps [32] . The synthetic approach commenced from a chiral homoallylic alcohol 12 b , which upon Prins cyclization with n ‐hexanal in the presence of trifluoroacetic acid followed by hydrolysis of the resulting trifluoroacetate provided the tri ‐substituted tetrahydropyran 210 (52 %).…”

Section: (4s6s)‐6‐hydroxy‐4‐undecanolide (2012)mentioning

confidence: 99%

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Synthetic Applications of Prins Cyclization in Natural Product Syntheses

Tadiparthi

Roy

Sakirolla

et al. 2022

The Chemical Record

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The natural products having tetrahydropyran unit with multiple chiral centers serve as magnificent building blocks for various active pharmaceutical ingredients (APIs). ‘Prins cyclization is one of the wonderful strategies to construct tetrahydropyran unit stereoselectively in asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various natural products from the past two decades (2005–2020) by using Prins cyclization as a key step. Further, the synthetic utility of this reaction was investigated and well demonstrated on various molecules successfully.

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Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Section: (4s6s)‐6‐hydroxy‐4‐undecanolide (2012)mentioning

confidence: 99%

Synthetic Applications of Prins Cyclization in Natural Product Syntheses

Tadiparthi

Roy

Sakirolla

et al. 2022

The Chemical Record

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Direct Room‐Temperature Lactonisation of Alcohols and Ethers onto Amides: An “Amide Strategy” for Synthesis

Valerio

Petkova

Madelaine

et al. 2013

Chemistry A European J

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Last‐minute deal: A direct lactonisation of ethers and alcohols onto amides that proceeds at room temperature under mild conditions is reported (see scheme). This allows the effective saving of up to two unproductive, sequential deprotection operations in synthetic sequences. Mechanistic studies are described, and a new “amide strategy” that exploits the dual robustness/late‐stage selective activation properties of this functional group is outlined.

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