The first stereoselective total synthesis of the Z-isomer of cytospolide E

Yadav, J. S.; Pandurangam, T.; Kumar, Alleni Suman; Reddy, Poli Adi Narayana; Prasad, A. R.; Reddy, B. V. Subba; Rajendraprasad, K.; Kunwar, A. C.

doi:10.1016/j.tetlet.2012.08.108

Cited by 11 publications

(17 citation statements)

References 16 publications

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“…Moreover, during the total synthesis of cytospolide P, we have observed that the presence of bulky allylic tert-butyldimethylsilyl (TBS) ether facilitated the formation of the E-selective RCM product. 4e Consolidating these facts and our own experiences, we planned the retrosynthesis of cytospolide E (5) as depicted in Scheme 1, where the role of protecting groups ought to be investigated with the goal of optimizing the best possible conditions allowing the total synthesis. Therefore, cytospolide E was planned to be synthesized from compound 7 via cyclic intermediate 6 using RCM as one of the key steps.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…They successfully constructed the 10-membered macrocycle over a possible 9-membered macrocycle in moderate yield. Therefore, we sketched the retrosynthesis of cytospoilde E (5) as depicted in Scheme 7, which could be synthesized from seco acid 39 where only the C-3 hydroxy would be suitably protected. Seco acid 39 could be constructed from compound 41 via intermediate 40 using modified Crimmins aldol as one of the key steps.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…A number of synthetic reports on cytospolides D and E exist in the literature. Yadav, 5 Nanda, 6 and Ramana 7 et al have shown, separately, the synthesis of Z-isomer of cytospolide E using the late-stage ring-closing metathesis (RCM)-based macrocyclization strategy. The Z-isomer of cytospolide D was also synthesized by Kamal 8 and Nanda 6 et al using the RCM approach.…”

Section: Introductionmentioning

confidence: 99%

“…Cytospolide E (5) having a C-2 methyl group of (S)-configuration is more toxic (IC 50 ∼ 10 μM) to human lungs carcinoma cell line A549 compared with cytospolide D (4), in which the C-2 methyl center is in the opposite configuration. 3 In continuation of our program 4 toward the asymmetric synthesis of bioactive macrocyclic natural products and their analogues, we embarked on the total synthesis of cytospolide E (5). A number of synthetic reports on cytospolides D and E exist in the literature.…”

Section: ■ Introductionmentioning

confidence: 99%

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Studies Directed toward the Stereoselective Synthesis of Cytospolide E

2018

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Our exhaustive effort toward the total synthesis of cytotoxic marine nonanolide cytospolide E has been detailed. To achieve this synthesis, we have explored both the ring-closing metathesis and lactonization-based macrocyclization strategies using a variety of precursors. Unfortunately, none of them provided the desired product. The ring-closing metathesis approach provided mainly the macrocycle with Z-olefin, whereas the macrolactonization strategy culminated in 8- epi -9- epi -cytospolide E following the regioselective formation of a 10-membered macrocycle over a 9-membered macrocycle.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Studies Directed toward the Stereoselective Synthesis of Cytospolide E

2018

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“…These compounds have shown antitumor activities. The first total synthesis of the Z-isomer of cytospolide E 178, based on Evans aldol reaction, Sharpless kinetic resolution, and RCM, was reported in 2012 by Yadav and coworkers (Scheme 63) [235].…”

Section: Ten-membered Lactonesmentioning

confidence: 99%

Metathetic Synthesis of Common and Medium-Sized Lactones: The State of the Art

Bassetti

D’Annibale

2015

Topics in Heterocyclic Chemistry

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Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (Z)‐Cytospolides D, E and Their Stereoisomers

Rej

Nanda

2013

Eur J Org Chem

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Chemoenzymatic asymmetric total synthesis of the (Z)‐isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring‐closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was accessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase‐catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2‐methyl‐1,3‐propanediol and Corey–Bakshi–Shibata (CBS) mediated stereoselective carbonyl reduction.

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The first stereoselective total synthesis of the Z-isomer of cytospolide E

Cited by 11 publications

References 16 publications

Studies Directed toward the Stereoselective Synthesis of Cytospolide E

Studies Directed toward the Stereoselective Synthesis of Cytospolide E

Metathetic Synthesis of Common and Medium-Sized Lactones: The State of the Art

Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (Z)‐Cytospolides D, E and Their Stereoisomers

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