State Key Laboratory of Elemento-organic Chemistry, College of Chemistry , Nankai University , Tianjin 300071 , China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071 , China.
J Org Chem. 2018 May 18;83(10):5825-5828. doi: 10.1021/acs.joc.8b00505. Epub 2018 May 2.
Concise total syntheses of (-)-(1 R,6 S,7 S,10 R)-hydroxycadinan-3-en-5-one (1), (+)-(1 R,5 S,6 R,7 S,10 R)-cadinan-3-ene-1,5-diol (2), and (+)-(1 R,5 S,6 R,7 S,10 R)-cadinan-4(11)-ene-1,5-diol (3), three cadinane sesquiterpenes sharing identical trans-decalin carbon skeletons yet containing different oxidation states and substitution patterns, are reported. They were prepared from a common trans-decalin intermediate, which was readily prepared on gram scale through an aldol-Henry reaction cascade and oxidation sequence.
(-)-(1R,6S,7S,10R)-羟基卡丹烷-3-烯-5-酮（1）、(+)-(1R,5S,6R,7S,10R)-卡丹烷-3-烯-1,5-二醇（2）和(+)-(1R,5S,6R,7S,10R)-卡丹烷-4(11)-烯-1,5-二醇（3）这三个共享相同的反式十氢萘碳骨架但具有不同氧化态和取代模式的卡丹烷型倍半萜的简洁全合成被报道。它们由一个共同的反式十氢萘中间体制备得到，该中间体可通过醛醇-Henry 反应级联和氧化序列以克级规模制备。
