Stereoselective Total Synthesis of Attenols A and B

Yadav, J. S.; Reddy, Poli Adi Narayana; Reddy, Y. Jayasudhan; Meraj, Syeda; Prasad, A. R.

doi:10.1002/ejoc.201300623

Cited by 18 publications

(8 citation statements)

References 24 publications

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“…An alternative strategy for the synthesis of 4 was developed so as to avoid a cumbersome continuous extraction step of a triol associated with the established method, in addition to improving the overall yield. The first step involved esterification of malic acid using methanol, followed by selective reduction of the resulting dimethyl ester using borane dimethyl sulfide (BMS) yielding diol 5 ( Scheme 2 ) [ 1 , 14 – 15 ].…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of ent-pavettamine

Zimuwandeyi¹,

Fernandes²,

Rousseau³

et al. 2021

Beilstein J. Org. Chem.

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Pavettamine, a plant toxin first isolated from Pavetta harborii in 1995, was previously identified as a polyamine with C2 symmetry and a 1,3-syn-diol moiety on a C10 carbon backbone – one of very few substituted polyamines to be isolated from nature. Its absolute configuration was later established by our first reported total synthesis in 2010. Herein we report the first total synthesis of the enantiomer of pavettamine, ent-pavettamine. The symmetrical structure of the molecule allows for the synthesis of a common C5 fragment that can be divergently transformed into two synthons for later convergent coupling to furnish the target carbon framework. Based on the success of the protocol we employed for the synthesis of the naturally occurring pavettamine, (S)-malic acid was again the starting material of choice for the synthesis of the two individual C5 fragments, with strategic differences in terminal-group manipulation allowing for the synthesis of ent-pavettamine rather than pavettamine. Chain extension and stereoselective ketone reduction were achieved using the (R)-methyl p-tolyl sulfoxide chiral auxiliary to give the desired 1,3-syn-diol C5 unit. A protecting-group strategy was also developed for the orthogonal protection of the alcohol and amine functional groups as they were unveiled. The functionalized C5 fragments were coupled via reductive amination revealing the C10 carbon backbone. Deprotection of the alcohol and amine functional groups successfully provided ent-pavettamine as a TFA salt.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of ent-pavettamine

Zimuwandeyi¹,

Fernandes²,

Rousseau³

et al. 2021

Beilstein J. Org. Chem.

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“…The generated spiroacetal 188 aer functional group transformations gave attenol A, 123 (Scheme 72). 83 Yadav and co-workers discussed the stereoselective synthesis of the spiroketal fragment of the immune suppressant (À)-ushikulide A, 127. The key feature of this synthesis involved the construction of the spiroketal moiety, which was formed by the subsequent hydrolysis of a dialkylated TosMIC 126 derivative that is generated from monoalkylated TosMIC 125 (alkylation of TosMIC 1a) with suitably substituted iodohydrin derivatives 124 (Scheme 73).…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Arylsulfonylmethyl isocyanides: a novel paradigm in organic synthesis

2015

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“…Given the scarcity of 1 coupled with its anticancer activity and our long-standing interest in the synthesis of 1,6-dioxaspiro[4.5]decane and 1,7-dioxaspiro[5.5]undecane moiety containing molecules, we embarked on the total synthesis of 1 to enable additional biological evaluation. Herein, we report the total synthesis of EBC-23 ( 1 ) by two divergent approaches from three simple building blocks.…”

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confidence: 99%

Total Synthesis of Anticancer Agent EBC-23

Reddy

Sabitha²,

Rao³

et al. 2016

Org. Lett.

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Total synthesis of spiroketal EBC-23 has been described by two divergent approaches from three simple building blocks. Gold-catalyzed cycloisomerization of alkynol and acid-mediated spirocyclization of diketalketone were successfully utilized to effect spiroketal formation. A Cu(I)-P(Cy)3-catalyzed protocol for the highly regio- and stereocontrolled hydroboration of internal propargylic alcohol was effectively applied toward the β-hydroxy ketone via vinylboronates.

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Stereoselective Total Synthesis of Attenols A and B

Cited by 18 publications

References 24 publications

Total synthesis of ent-pavettamine

Total synthesis of ent-pavettamine

Arylsulfonylmethyl isocyanides: a novel paradigm in organic synthesis

Total Synthesis of Anticancer Agent EBC-23

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