Total synthesis of (−)-clavosolide A

Chakraborty, Tushar Kanti; Reddy, Vakiti Ramkrishna; Gajula, Praveen Kumar

doi:10.1016/j.tetlet.2006.08.055

Cited by 27 publications

(22 citation statements)

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“…Based on our conclusions on the effect of substitution on Macrodiolides molecules, we chose a series of Macrodiolides derivatives; some of them have a biological activity [52][53][54][55][56][57][58][59][60]. Initially, we performed a structural comparison of this series Figure 4.…”

Section: Structural Comparison Of the 16-membered Macrodiolidesmentioning

confidence: 99%

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Mazri

Belaidi

Kerassa

et al. 2014

ILCPA

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Electronic structures, Conformational Analysis, effect of the substitution and structure activity Relationships for macrodiolides, have been studied by PM3 and ab initio methods. In the present work, the calculated values, namely net charges, bond lengths, MESP, dipole moments, electronaffinities, heats of formation, drug-likeness and QSAR properties, are reported and discussed in terms of the biological activity of macrodiolides.

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Section: Structural Comparison Of the 16-membered Macrodiolidesmentioning

confidence: 99%

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Mazri

Belaidi

Kerassa

et al. 2014

ILCPA

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“…8 Willis also proposed a revised structure 5 for the natural clavosolide A 5 and our group confirmed the relative stereochemistry of clavosolide A (5) by stereoselective total synthesis ( Figure 2). 8a Subsequently, Smith,9 Willis, 10 and Chakraborty 11 unambiguously determined the absolute stereochemistry of (-)-clavosolide A (5) by comparison of the optical rotation.…”

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confidence: 99%

Enantioselective Total Synthesis of (-)-Clavosolide A and B

Son¹,

Kim²,

Kim³

et al. 2010

Bulletin of the Korean Chemical Society

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Enantioselective total synthesis of (-)-clavosolide A and B was reported in full including the synthesis of proposed structure of (-)-clavosoldie A (1), revised structure of (-)-clavosoldie A (5), and revised structure of (-)-clavosoldie B (6). The relative and absolute stereochemistries of the natural products were confirmed unambiguously by comparing the optical rotation values and 1 H and 13 C NMR spectra of them.

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“…The prelinimary experiments used racemic material which was prepared by the method of Luche. 47 In an early attempt using Cardillo's procedure, the deprotonation of the alcohol (rac- 85) was carried out by addition of n-BuLi. Subsequent treatment of CO 2 resulted in the fomation of a hemi carbonate anion which was then subjected to reaction with I 2 in THF (Scheme 47b, a).…”

Section: Resultsmentioning

confidence: 99%

“…Unfortunately the propargylic alcohol (215) with the wrong configuration was delivered as the major product. Therefore the alcohol (215) had to be converted to the desired configuration (216) by the Mistunobu reaction 82,…”

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Synthesis of natural products by intramolecular Michael addition

Song¹

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Scheme 5a Reagents and conditions: (a) TsCl, N,N-dimethylaminopyridine, CH 2 Cl 2 , 97%; (b) PrMgBr, Li 2 CuCl 4 , THF, 87%; (c) HCl, MeOH, 55 o C, 98%; (d) Me 2 NCH(OMe) 2 , 70 o C; (e) Ac 2 O, CH 3 CN, reflux, 70% for two steps. The addition proceeded selectively giving the 1,3-trans isoxazolidine (38) as the main isomer. Use of zinc delivered the ring opened amino alcohol (40) which was then converted to the corresponding ketone (41) using Wacker oxidation. Tandem intramolecular condensation-hydrogenation was carried out to give the 2,6-cis-piperidine (42) ring (via an iminium ion) as the only isomer. The hydroxy group was then activated by mesylation and the subsequent intramolecular S N 2 substitution helped to construct the bicycle. Finally, nucleophilic displacement followed by reductive deiodination was carried out to accomplish the synthesis of (+)-monomorine I (Scheme 5b). The key step for this synthesis is the intramolecular condensation which built up the proper stereogenic centers and carbon framework of the final product. The disadvantage of the synthesis is the introduction of too many oxygen atoms which makes the route unnecessarily long due to the need for extra steps to remove functionality.

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Total synthesis of (−)-clavosolide A

Cited by 27 publications

References 27 publications

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Enantioselective Total Synthesis of (-)-Clavosolide A and B

Synthesis of natural products by intramolecular Michael addition

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