@article {48355,
	title = {Concise total synthesis of (+)-lanceolactone a: revision of absolute stereochemistry},
	journal = {Journal of Organic Chemistry},
	volume = {87},
	year = {2022},
	month = {OCT},
	pages = {12867-12876},
	type = {Article},
	abstract = {<p>
	A chiral-pool protecting-group-free five-step total synthesis of tetranorsesquiterpenoide (+)-lanceolactone A and all of its four stereoisomers using (S)-(+)-, and (R)-(-)-linalool (coriandrol) as building blocks is disclosed. The key steps involved in this synthetic route are regioselective ozonolysis, Au(I)-catalyzed cycloisomerization-induced construction of furan from alleneone, and dye-sensitized photo-oxidation (through O-1(2) ; singlet oxygen) of hydroxyalkyl-tethered furan to access oxaspirolactone. After a thorough evaluation of electronic circular dichroism (ECD) and optical rotation data of all possible stereoisomers, the absolute configuration of natural lanceolactone A at the C4 and C7 positions has been assigned as (+)-(4S,7S), which is an enantiomer to the initially proposed structure (+)-(4R,7R). Further, these investigations led us to extend Feringa and Gawronski{\textquoteright}s CD correlation method to [5,5]- and [6,5]-oxaspirolactones.</p>
},
	issn = {0022-3263},
	doi = {10.1021/acs.joc.2c01450},
	author = {Borade, Balasaheb R. and Kontham, Ravindar}
}
