. The Study of Resource Chemistry[J]. Progress in Chemistry, 2010, 22(04): 537-556.
This review summarize our research progress in resource chemistry, which related to the reaction of steroidal sapogenin (natural resource compound) and fluoroalkanosulfonyl fluoride (non-natural one) as well as their application in organic synthesis. The strategies and tactics of utilizing steroidal sapogenin in “atom economy” way are introduced in the first paragraph. For solving the environmental pollution and resource waste generated in the industrial utilization of steroidal sapogenin, our group developed new method that using 30% commercial H2O2 instead of CrO3 to oxidize pseudo-sapogenin, which made it is possible to the 100% utilization of the steroidal sapogenin resource. Direct oxidization of steroidal sapogenin with the per-acid generated in situ starting from 30% commercial H2O2 and acid to produce pregna-16,20-diol type compound and 4R-methyl δ-valerolactone. Iodine induced abnormal Baeyer-Villiger rearrangement of sapogenin provided steroidal 16-hydroxyl-22-lactone and 3R-methyl γ-butyrolactone. All of their degraded products have been applied in the synthesis of some steroidal medicine, insect hormone, perfume and natural product. The strategy of using intact skeleton of steroidal sapogenin to synthesize target molecule are also described. In second paragraph, the strategies and tactics of utilizing fluoroalkanosulfonyl fluoride are introduced. To make reaction symbiosis is a new ideal in order to enhance the utilization ratio of the resource compound. We explore symbiotic reactions of vicinal diol epoxidation, alkene epoxidation and carbocation rearrangement with fluoroalkanosulfonyl fluoride hydrolysis based on this concept. The synthetic application of such reactions is also presented in this review.
Contents
1 Resource chemistry and resource compound
2 Resource chemistry based on natural resource compound steroidal sapogenin
2.1 Steroidal sapogenin: origination, utilizing way and problems remained
2.2 The clean oxidative degradation of steroidal sapogenin
2.3 The reaction of the degradation products of steroidal sapogenin and their application in organic synthesis
2.4 The synthesis of natural sterols by using the intact skeleton of steroidal sapogenin
3 Resource chemistry based on non-natural resource fluoroalkanosulfonyl fluoride
3.1 The reaction of fluoroalkanosulfonyl fluoride and its application in Epristeride synthesis
3.2 The symbiotic reaction of fluoroalkanosulfonyl fluoride hydrolysis and 1,2-diol epoxidation
3.3 The symbiotic reaction of fluoroalkanosulfonyl fluoride hydrolysis and alkene epoxidation
3.2 The symbiotic reaction of fluoroalkanosulfonyl fluoride hydrolysis and carbocation rearrangement