Synthesis and [4 + 2]-annulation of enantioenriched (z)-crotylsilanes: preparation of the C1-C13 fragment of bistramide A.
[reaction: see text]. New chiral crotylsilanes that bear a (Z)-olefin geometry were synthesized in high enantiopurity. The reagents participate in [4 + 2]-annulations with aldehydes to give stereochemically complementary pyrans (relative to (E)-crotylsilanes) bearing 2,6-cis-5,6-cis and 2,6-trans-5,6-cis relationships of peripheral functionalities. A stereoselective synthesis of the C1-C13 fragment of bistramide A is also described highlighting this annulation strategy.
Lowe
Jason T
JT
Department of Chemistry, Boston University, Massachusetts 02215, USA.
Panek
James S
JS
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000081:Acetamides; D011714:Pyrans; D012821:Silanes; D013141:Spiro Compounds; C059975:bistratene A