A chemoenzymatic asymmetric synthesis of (+)-strictifolione

Ghadigaonkar, Sneha; Koli, Mrunesh; Gamre, Sunita; Choudhary, Manoj K.; Chattopadhyay, Subrata; Sharma, Anubha

doi:10.1016/j.tetasy.2012.06.015

Cited by 15 publications

(10 citation statements)

References 53 publications

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“…Among several synthetic methods for the construction of 1 , 6 notable streamlined efforts have recently been made. In 2003, Cossy and coworkers developed a concise and elegant synthetic pathway consisting of a longest linear sequence of 9-steps, starting from 3-phenyl-propionaldehyde, that utilized the dual use of enantioselective allyltitanation in conjunction with cross metathesis (CM).…”

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confidence: 99%

“…In 2003, Cossy and coworkers developed a concise and elegant synthetic pathway consisting of a longest linear sequence of 9-steps, starting from 3-phenyl-propionaldehyde, that utilized the dual use of enantioselective allyltitanation in conjunction with cross metathesis (CM). 6a In 2010, Das and coworkers devised a comparable pathway with an LLS of 10-steps using Sharpless kinetic resolution and olefin cross-metathesis. 6g In 2010, She and coworkers 6h developed an efficient route employing a one-pot, double allylboration comprised of a pathway with a 7-step LLS using an Ipc 2 BH-derived boryl-substituted allylborane, derived in two steps from propargyl bromide, 7 3-butenal, derived in two steps from glyoxal, and a ketal- protected aldehyde.…”

mentioning

confidence: 99%

“…6a In 2010, Das and coworkers devised a comparable pathway with an LLS of 10-steps using Sharpless kinetic resolution and olefin cross-metathesis. 6g In 2010, She and coworkers 6h developed an efficient route employing a one-pot, double allylboration comprised of a pathway with a 7-step LLS using an Ipc 2 BH-derived boryl-substituted allylborane, derived in two steps from propargyl bromide, 7 3-butenal, derived in two steps from glyoxal, and a ketal- protected aldehyde. 8 Despite significant attributes of these syntheses, 6 the development of simple, efficient, scalable strategies that are library amenable for installation of key diversity elements in a divergent manner, is notably absent in the literature.…”

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confidence: 99%

“…6g In 2010, She and coworkers 6h developed an efficient route employing a one-pot, double allylboration comprised of a pathway with a 7-step LLS using an Ipc 2 BH-derived boryl-substituted allylborane, derived in two steps from propargyl bromide, 7 3-butenal, derived in two steps from glyoxal, and a ketal- protected aldehyde. 8 Despite significant attributes of these syntheses, 6 the development of simple, efficient, scalable strategies that are library amenable for installation of key diversity elements in a divergent manner, is notably absent in the literature. In this regard, multi-reaction one-pot protocols have emerged as powerful synthetic strategies to achieve total/intermediate/analog synthesis, due to the ability to form multiple bonds and stereocenters, while invoking step, atom, 9, green and pot economy, 10 thus saving time and resources.…”

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confidence: 99%

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An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product

2013

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An efficient, library amenable, “pot economical” total synthesis of (+)-strictifolione and the related natural product, (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2H-2-pyrone are reported. This modular approach takes advantage of two consecutive phosphate tether-mediated, one-pot, sequential protocols, followed by a final cross metathesis to deliver both antifungal natural products in a three-pot process from the respective enantiomeric (R,R)- and (S,S)-trienes with minimal purification. A salient feature of this route is that additional protecting groups are not required as a result of the orthogonal protecting- and leaving-group properties innate to phosphate triesters.

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An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product

2013

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“…Its earlier syntheses were mentioned by Macro et al [12]. Recently, a large number of new syntheses of strictifolione (176) have been reported [92,[103][104][105][106][107][108][109].…”

Section: Strictifolionementioning

confidence: 98%

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

et al. 2020

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Pyranone natural products have attracted great attention in recent years from chemists and biologists due to their fascinating stereoisomeric structural features and impressive bioactivities. A large number of stereoselective total syntheses of these compounds have been described in the literature. The natural pyranones with long side chains have recently received significant importance in the synthetic field. In the present article, we aim to review the modern progress of the stereoselective total syntheses of these natural pyranones containing long-chain substituents.

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Alkene Cross‐Metathesis Reactions

et al. 2021

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This chapter describes olefin cross‐metathesis (CM) reactions catalyzed by ruthenium, molybdenum, and tungsten complexes and surveys the literature from 1993 through 2020. Cross‐metathesis has been applied to the synthesis of a wide range of functionalized alkenes, including natural and biologically active products. Due to its simplicity and inherit atom economy, CM has found applications in the preparation of fine chemicals and various building blocks, and in transformations of biomass. Tandem reactions involving CM as the key step are also reviewed. Examples discussed in this chapter serve to illustrate how the reactivity of alkene substrates in CM depends on the presence of functional groups and steric congestion in the proximity of the reacting double bonds. A discussion of the mechanism of olefin metathesis is also included.

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A chemoenzymatic asymmetric synthesis of (+)-strictifolione

Cited by 15 publications

References 53 publications

An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product

An Efficient, Modular Approach for the Synthesis of (+)-Strictifolione and a Related Natural Product

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

Alkene Cross‐Metathesis Reactions

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