122052-54-4Relevant academic research and scientific papers
Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis
Liffert, Raphael,Linden, Anthony,Gademann, Karl
, p. 16096 - 16099 (2017)
The first enantioselective total synthesis of the complex tricarbocyclic sesquiterpenoid periconianone A based on a postulated biogenesis is reported. Key elements of the synthetic route include the use of an isopropenyl group as a removable directing group for stereoselective synthesis, a sequence featuring a Rh-mediated O-H insertion/[3,3]-sigmatropic rearrangement and subsequent α-ketol rearrangement, and a late stage aldol reaction to furnish the complex cage-like framework.
Hydrodealkenylative C(sp3)–C(sp2) bond fragmentation
Smaligo, Andrew J.,Swain, Manisha,Quintana, Jason C.,Tan, Mikayla F.,Kim, Danielle A.,Kwon, Ohyun
, p. 681 - 685 (2019/06/11)
Chemical synthesis typically relies on reactions that generate complexity through elaboration of simple starting materials. Less common are deconstructive strategies toward complexity—particularly those involving carbon-carbon bond scission. Here, we introduce one such transformation: the hydrodealkenylative cleavage of C(sp3)–C(sp2) bonds, conducted below room temperature, using ozone, an iron salt, and a hydrogen atom donor. These reactions are performed in nonanhydrous solvents and open to the air; reach completion within 30 minutes; and deliver their products in high yields, even on decagram scales. We have used this broadly functionality tolerant transformation to produce desirable synthetic intermediates, many of which are optically active, from abundantly available terpenes and terpenoid-derived precursors. We have also applied it in the formal total syntheses of complex molecules.
EFFICIENT SYNTHESIS OF NATURAL ENANTIOMER OF SPOROGEN-AO 1 (13-DESOXYPHOMENONE), A SPOROGENIC SESQUITERPENE FROM ASPERGILLUS ORYZAE
Kitahara, Takeshi,Kurata, Hitoshi,Mori, Kenji
, p. 4339 - 4350 (2007/10/02)
An efficient total synthesis of (+)-sporogen-AO 1 (13-desoxyphomenone) 1 was achieved in 20 steps from ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate 3 in 8.3percent overall yield.The optically active 3 with 98.4percent e.e. was easily ob
