The second stereoselective total synthesis of (–)-hedycoropyran A (1) has been accomplished in 10 steps with 4.73% overall yield from the readily available alkene 6. The key features of our strategy include (1) highly diasteoreoselective construction of trans-2-alkyl-6-aryl-3,6-dihydro-2H-pyran framework and (2) substrate-controlled trans-dihydroxylation at C(3)/C(4)