A Flexible Route to [4.1.1]Propellanes

The Natural Products Chemistry of Cyanobacteria

“…30 However, in this latter regard it is surprising that not more synthetic effort has been expended in the synthesis of malyngamide derivatives as there are many features of structural interest, 31 and some malyngamides possess biomedically useful properties such as cancer cell cytotoxicity 32 and anti-HIV properties. 35 Grenadamide was moderately active in a brine shrimp toxicity model. 34 The structures of these two metabolites were developed from normal nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, and subsequently, asymmetric synthesis of grenadamide showed it to possess the R configuration at both chiral centers.…”

“…96 Two oxidized derivatives, lyngbyatoxins B (35) and C (36), were reported in 1990 from another L. majuscula specimen collected from the same beach as the initial lyngbyatoxin A producer. 96 Two oxidized derivatives, lyngbyatoxins B (35) and C (36), were reported in 1990 from another L. majuscula specimen collected from the same beach as the initial lyngbyatoxin A producer.…”

Recent Advances in Cyclopropene Chemistry

“…144 The Diels-Alder reaction of cyclopropene 134 was employed by Baird in the synthesis of propellane 137. 146 Thus, cycloadduct 136, obtained by reaction of 134 with isobenzofuran 135, 147 was subjected to 1,3-elimination with n-butyllithium to form 137 in good yield (Scheme 83).…”

Intramolecular Cyclopropene-Furan [2 + 4] Cycloaddition followed by a Cyclopropylcarbinyl Rearrangement to Synthesize the BCD Rings of Cortistatin A

“…9 Similarly, Baird trapped 1-cyclopropene carbinol with furan (rt) to give 10 and 11 (1:2). 10 It appears that the usual endo kinetic preference is eroded by the extremely exothermic relief of cyclopropenyl ring strain in the transition state leading to the Diels-Alder adducts.…”