Convergent Total Synthesis of (+)-Cotylenin A

Uwamori, Masahiro; Osada, Ryunosuke; Sugiyama, Ryoji; Nagatani, Kotaro; Nakada, Masahisa

doi:10.1007/978-981-16-2458-2_7

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2023

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“…We have previously observed that the enolate formed by the reaction of β-keto sulfone using a reductant such as samarium iodide exhibits poor reactivity toward electrophiles. 9 However, gratifyingly, the treatment of 12 with lithium naphthalenide and the subsequent reaction with methyl cyanoformate afforded 13 in 90% yield (Scheme 4 ). 10…”

Section: Table 1 Comparison Of the 1 ...mentioning

confidence: 99%

Enantioselective Formal Total Synthesis of Damsin

Sugiyama¹,

Nakada²

2023

Synlett

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Enantioselective formal total synthesis of damsin, which was isolated from Compositae Ambrosia maritima L., is described. The highly enantio- and diastereoselective catalytic Mukaiyama-Michael reaction and subsequent highly stereoselective epimerization shorten the synthetic steps. It is also reported that the enolate, which was formed by the reaction of β-keto sulfone with lithium naphthaenide, reacted with methyl cyanoformate to form a quaternary stereogenic center in high yield with high stereoselectivity. This finding extends the synthetic chemistry starting from β-keto sulfones.

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Section: Table 1 Comparison Of the 1 ...mentioning

confidence: 99%